Our Sweet Adventures

The Best Charlottesville Wineries on the Monticello Wine Trail

The Best Charlottesville Wineries on the Monticello Wine Trail

Did you know that Virginia is the birthplace of American wine? Yes, not California… Virginia! With that said, Virginia has over 300 wineries. So with all of the wineries to explore in such little time, we recommend going to the heart of Virginia’s wine country on the Monticello Wine Trail.

Why? Because the best wineries in Charlottesville, if not, the entire state of Virginia, can be found on the Monticello Wine Trail. There are 33 wineries on the Monticello Wine Trail that all span near the Blue Ridge Mountains.

The Blue Ridge Mountains and Charlottesville are two of the best places to visit in Virginia . So with a great glass of wine and the vibrant Blue Ridge Mountains, you can guarantee you will be surrounded by great beauty.

Thus, making the Charlottesville wineries on the Monticello Wine Trail, a great destination on an East Coast road trip . You can even turn your trip to a romantic getaway and stay at a winery bed and breakfast .

Here are five of the best Charlottesville wineries that should include in your weekend itinerary .

Full disclaimer –  We received complimentary wine tastings, dining, and accommodation during our trip to Monticello Wine Trail. As always, our opinions are non-biased and our own. We want to thank the wineries we worked with for their generosity. In addition, we want to thank everyone for following and supporting us on all of Our Sweet Adventures. 

Veritas Winery and Vineyard

Veritas Winery and Vineyard was our absolute favorite winery for several reasons. They have our favorite type of wine in the entire world, ice wine. In addition, they also have spectacular views of the Blue Ridge Mountains, offer wine tours and they have the most lovely bed and breakfast you can imagine.

We highly recommend this to be your last winery stop during your 2-day Monticello Wine Trail because staying at the Farmhouse at Veritas is an incredible experience. You can enjoy complimentary wines, champagne, a farm to table dinner, cozy accommodations and a delicious breakfast to continue your wine journey.

Loving our room with an awesome staircase at the Farmhouse at Veritas

In addition to the bed and breakfast, a visit to Veritas Winery and Vineyard is an incredible winery that should not be missed on the Monticello Wine Trail. It is truly one of the best Charlottesville Wineries, if not the world. We have never liked so many wines from the same winery before and we’ve been to plenty. During your visit to the winery be sure to enjoy their wine tasting. You will instantly fall in love with Veritas wide selection of beautiful wines as we did.

Furthermore, you should also enjoy their wine tour where you can learn about the history of the owners and property itself. If you are interested in the wine tour, be sure to call ahead and make reservations for it. Lastly, enjoy their patio that looks out to the vineyards with the Blue Ridge Mountains in the backdrop with a glass of wine and scrumptious appetizers. Their onsite restaurant, The Terrace, serves delectable sandwiches, salads, cheese, hummus and charcuterie.

Known For: Incredible views, delicious food, Starry Nights summer music series event and their B&B, the Farmhouse at Veritas.

Our Favorite Wines: Kenmar, White Star, Red Star, Club Cluvée and Rose 2017.

Tasting Price: Between 8-10 wine tastings for $10 per person. Group tastings of at least 8 people are $15 per person and reservations are required.

151 Veritas Lane Afton, VA 22920 (540) 456-8000 Mon – Fri: 9:30am – 5:30pm Sat – Sun: 11am – 5pm

Jefferson Vineyard

A visit to the Monticello Wine Trail cannot be complete without a visit to Jefferson Vineyard. The name of the estate says it all. The vineyard is rich with history from Thomas Jefferson and his close Italian friend and winemaker, Philip Mazzei. Together they helped create Virginia as the birthplace of American wine. Mazzei did everything he could to help bring Jefferson’s dream of American wine into a reality. Sadly it never went into fruition due to the vines being destroyed. However, Jefferson would be proud to see this land and vineyard has honored him admirably by producing fine wines.

The Jefferson Vineyard has been in the Woodward family for three generations. So guests can expect great care, passion and love brought into each bottle of wine. We certainly tasted these characteristics as the Jefferson Vineyard was one of our favorite wineries on the Monticello Wine Trail. What makes Jefferson Vineyard one of the best wineries in Charlottesville (besides taste), is their labels. As cat lovers, we are a little biased with one of them, since it has a cat on the label. The cat is made in memory to the owner’s cat, Sam. Furthermore, the more unique wine labels are a simple, naked bottle with Thomas Jefferson’s handwriting. It is by far the coolest wine bottle and very fitting being in the birthplace of America’s wine.

Visitors can enjoy three different wine tastings at Jefferson Vineyard – classic, private and library. The classic tasting offers eight wonderful wines. The library wine tasting is offered during select times of the year and provides their most premium award-winning library wines. The private tasting says it all, but also includes the eight classic wines in addition to two premium library wines.

Known For:  Rich history, incredible views and Virginia’s first Petit Verdot

Our Favorite Wines: Vin Blanc 2017, Chardonnay Reserve 2017 and Petit Verdot 2016

Tasting Price:  Classic tasting of 8 wines for $12 per person. For a private tasting, it must be booked in advanced and includes 10 wines (8 classic and 2 library) for $25 per person. Contact estate about the premium library tasting. Group tastings of at least 8 people are asked to contact the estate for arrangements. Guests get to take home a signature wine glass.

1353 Thomas Jefferson Parkway Charlottesville, VA 22902 (434) 977-3042 Open daily: 11am – 6:15pm

Early Mountain

Early Mountain is one of the best wineries in Charlottesville for tastings, great atmosphere, special event space and of course, their wine. Though there are several aspects that make Early Mountain stand out on the Monticello Wine Trail, it is their dedication to showcasing the best wine in Virginia. Early Mountain is committed to not only producing high-quality wine but to also promote Virginia as a world-class wine region. With that said, visitors can find a “Best of Virginia” wine selection in Early Mountain’s tasting room.

Furthermore, their dedication to supporting Virginia does not end with the wine. Early Mountain also features a full menu using produce from local farms, dairies and ranches. So when visitors come for the award-winning wine, they can pair it with delicious cuisine. Our three favorite must order items are the pimento cheese, Cubano and chicken salad sandwich. They were absolutely divine!

Enjoying the best pimento cheese at one of the best Charlottesville wineries

There is so much to enjoy during your visit to Early Mountain. Guest’s can enjoy the beautiful tasting room, or sit on the lovely patio soaking up the mountainous scenery. They can also ask about a wine tour and see the process of how Early Mountain produces their fabulous wines. Better yet, book a special event in their gorgeous event spaces. We were ready to renew our vows when we saw all of their private special event rooms. From a private cellar dining room to a grand ballroom – we were sold!

monticello wine trail tour

Known For:  Number one Tasting Room in America, “Best of Virginia” wine selection, patio with scenic views, delicious cuisine, year round events (concerts, festivals, dinners, classes) and special event space.

Our Favorite Wines “Young Wine” Vidal 2017, Stone Mountain Chardonnay 2016 and Eluvium 2014

Tasting Price:  Their wine tasting includes 6 of the current releases for $12 per person. The “Cheers tasting includes 6 of the current releases in addition to three of their precious wines for $18 per person. Group tastings of at least 15 people are asked to make reservations in a special event room. Guests get to take home a signature wine glass.

6109 Wolftown-Hood Road Madison, VA 22727 (540) 948-9005 Wed – Mon: 11am – 6pm Closed on Tuesdays

Barboursville Vineyards

Barboursville Vineyards is one of the most popular wineries on the Monticello Wine Trail because of its superb wines and rich history. The vineyard occupies the estate of James Barbour, Virginia’s Governor during the War of 1812. Furthermore, the vineyard’s estate also has the ruins of Governor Barbour’s mansion which was designed by Thomas Jefferson.

There is no better winery to get a grand wine tasting experience, than at Barboursville Vineyards. Guests who choose the classic tasting get to partake in almost 20 wine tastings! Starting with exquisite whites, to vibrant reds and finishing on a sweet note with dessert wines. Another amazing wine tasting experience is their Library 1821 which features a (always changing) selection of 20 flights of older vintages paired with bite-sized culinary fare.

The most popular and famous award-winning wine at Barboursville Vineyards is their Octagon wine. It is comprised of a beautiful blend of Merlot, Petit Verdot, Cabernet Franc, and Cabernet Sauvignon. For an additional price in the classic tasting, guests can enjoy an ounce of the Octagon. Or you can enjoy it during the Library 1821 tasting. We highly recommend it, as the Octagon is as brilliant as everyone says.

Barboursville Vineyard also has Palladio Restaurant which serves lunch and dinner to guests. As well as a 1804 Inn for guests to stay and enjoy the full Barbousville experience. It is truly an amazing place to escape and relax in Virginia’s wine country.

Known For:  Octagon wine, rich history and expansive wine tastings.

Our Favorite Wines: Pinot Grigio 2017, Barbera Reserve 2016, Octagon and Phileo.

Tasting Price:  Their wine tasting includes at least 17 of their current vintages for $7 per person. The Library 1821 tasting of older vintages paired with bite-sized culinary fare for $25 per person. Guests get to take home a signature wine glass.

17655 Winery Road Barboursville, Va 22923 (540) 832-3824 Mon – Sat: 10am – 5pm Sun: 11am – 5pm

Pippin Hill Farm

Pippin Hill Farm is exactly the experience we were wanting during our Monticello Wine Trail – good wine, delicious food, charming ambiance, and great views. What sets Pippin Hill Farm apart as one of the best wineries in Charlottesville, is their farm to table dining experience with the best views on the Monticello Wine Trail. We fell head over hills with Pippin Hill Farm the moment we drove through their vineyard. The entrance welcomes you with grapes hanging on the vineyards left and right as you drive through. Then you are greeted with a flowering hedge that takes you to stunning views of rolling mountains.

We instantly wanted to renew our vows (yes, again) at Pippin Hill Farm. So with that said, it is one of the most beautiful properties with a variety of special event space. One space that completely stole our hearts is their patio dining area. It is the perfect place to enjoy lunch and wine with your friends or loved ones.

monticello wine trail tour

Pippin Hill Farm is a family owned winery & vineyard that is committed to sustainable viticulture, farm to table dining experiences and supporting local farmers and producers. With that said, they have their own Chef’s Garden. Their menu at their Tasting Room includes a guide of what they grow and when they harvest each vegetable, fruit and herbs. Then the menu also informs you which entrees include produce from their Chef’s Garden. To continue the farm to table experience, guests can also take a stroll through the garden. The culinary journey does not end there, they also have their own free range chicken coop! So when you are looking to order an appetizer, I highly recommend the Deviled Eggs. They were heavenly!

Known For:  Farm to table dining experiences, cooking classes, incredible views, and a charming country ambiance.

Our Favorite Wines: Zero White 2017, Viognier 2017 and Merlot Reserve 2015.

Tasting Price:  Their Classic Tasting includes five wines for $10 per person. The Reserve Tasting includes four of their vintage wines for $13 per person. Guests can take home a signature wine glass for $1.

5022 Plank Road North Garden, VA 22959 (434) 202-8063 Tues – Sun: 11am – 5pm Closed on Mondays

I hope I have inspired you to take a trip to the heart of Virginia’s wine country. As you can see, these are truly some of the best wineries with unique and amazing experiences along the Monticello Wine Trail! It is without a doubt, the perfect getaway to savor fantastic wines and delicious farm to table dining experiences.

A visit to the best Charlottesville wineries is the perfect romantic getaway for couples. Beautiful views, fabulous wines, delicious cuisine, B&B and more.

Sign me up for the newsletter!

Notify me of follow-up comments by email.

Notify me of new posts by email.

Michelle Dodson

Monday 5th of September 2022

Can't wait to visit next week!


I hope you enjoy!!!! All the wineries are lovely with some amazing views :)

Experience a Winery, Wine Vineyard or Wine Tasting While Traveling

Tuesday 22nd of October 2019

[…] Monticello wine trail in Virginia is a beautiful one to experience on the east coast of United States! […]

10 Fun Things to Do in Washington D.C. in the Fall - A Local's Guide

Thursday 12th of September 2019

[…] there are so many amazing wine countries just outside of D.C. From the Loudoun County to the Monticello Wine Trail in Charlottesville, Middleburg County, the Piedmont Trail in Maryland, and more – you could easily drink wine […]

The 8 Best Wineries in Fredericksburg, Texas - Weekend Guide

Tuesday 13th of August 2019

[…] Cabernet Sauvignon, Merlot, Malbec, and Viognier. (Fun fact: we first had Viognier wine when visiting wineries in Charlottesville, Virginia.) With that said, though the Texas Hill Country is the largest wine region in Texas, 80% of the […]

Becca Talbot

Sunday 4th of November 2018

You know, I've never done a wine tasting tour - and it's something I'd absolutely love to do! I had no idea Virginia was the birth place of wine in the US, ha! Learn something new every day ;) x

The Thought Card

Explore the Monticello Wine Trail in Virginia

Monticello Wine Trail in Charlottesville Virginia

Inspired by Thomas Jefferson’s bold dream to create vineyards near his home in Virginia, the Monticello Wine Trail consists of over 30 wineries that produce some of the highest-quality grapes and wines in the world. Only an hour away from Richmond, Virginia, spend the day on the Monticello Wine Trail in Charlottesville, home to the celebrated wineries and vineyards of the Blue Ridge Mountains. On the Monticello Wine Trail, explore Virginia’s bucolic countryside. Sample the regional wine from some of the best Charlottesville wineries, meet the winemakers, and take in Virginia’s rich cultural history. With many vineyards and wineries to choose from, this shortlist includes historic vineyards, wineries and a cidery.

And while I’m not encouraging anyone to travel right now during the crisis, consider visiting this beautiful region when the experts say that it is safe to do so.

Monticello Wine Trail: Wineries in Charlottesville

Table of Contents

An Easy Day Trip From Richmond, Virginia

Early mountain vineyards, jefferson vineyards, bold rock cidery , glass house winery, pippin hill farm & vineyards, thatch winery, trump winery , where to stay in richmond.

Early Mountain Vineyards is an esteemed 55-acre vineyard in Madison, Virginia. This small town has only 221 residents and sits comfortably in the lush green pastures of the foothills of the Blue Ridge Mountains. Its picturesque scenery is nothing short of stunning, and it might even make you forget about visiting the other surrounding Monticello wineries and vineyards.

  A post shared by Early Mountain Vineyards (@earlymountain) on Oct 10, 2015 at 2:09pm PDT

Early Mountain Vineyards offers award-winning wines that are known for historical consistency. They also serve a full menu of wine-friendly foods including artisanal cheese, fresh pasta, salads, and sandwiches. All of the food comes from local farms and dairies.

  A post shared by Early Mountain Vineyards (@earlymountain) on Apr 12, 2016 at 11:14am PDT

Early Mountain Vineyard Address: 6109 Wolftown-Hood Rd, Madison, VA 22727

“In 1774, Thomas Jefferson and Italian Filippo Mazzei established vineyards on land adjoining Monticello, the site of present-day Jefferson Vineyards, Virginia’s premiere small production winery.” – Jefferson Vineyards . Almost 250 years later, the tradition of Jefferson Vineyards lives on.

This charming vineyard offers more than just a presidential reputation and a fabled legacy. It also boasts savory wines and has one of the best pastoral views in Charlottesville, Virginia. This family owned winery feels like a scene out of a Faulkner novel. From any spot on the property, marvel at the beautiful foliage that’s unique to the Blue Ridge Mountains.

While relishing in the splendor of the vineyard, don’t forget to enjoy the vineyard’s award-winning Pinot Gris, Chardonnay, Riesling, Viognier, Merlot or Cabernet Franc. The Estate Reserve and Virginia’s first Petit Verdot are also excellent choices.

Jefferson Vineyards Address: 1353 Thomas Jefferson Pkwy, Charlottesville, VA 22902

Founded in June of 2012, Bold Rock has become one of the nation’s largest independently-owned cider companies. Unlike the other locations on this list, Bold Rock specializes in hard cider, which is fermented apple juice. Since the apples are grown close by, they pick the apples at the peak of their freshness and extract 85 percent of the apple’s juice for the cider.

The Carter Mountain Orchard is just minutes outside of Charlottesville, Virginia. It has breathtaking scenic views, and you can enjoy the unique experience of picking your own fruit in the apple orchard. They also offer tastings, space for private events, and trendy merchandise. Since this is a seasonal location, check the website for the latest hours. 

Carter Mountain Orchard Address: 1435 Carters Mountain Trail Charlottesville, VA 22902

The Glass House Winery’s attached temperature-controlled glass conservatory provides a relaxing space to enjoy the tropical foliage, handmade chocolates and wines. There’s also a deck overlooking the lake and picnic tables.

While exploring the tropical ambiance and decor, pair some of Michelle’s mouth-watering chocolates like the Red Wine Cream Chocolate or the Salted Caramel Chocolate with Jeff’s award-winning 2015 Viognier or 2014 Cabernet Franc.

Glass House Winery Address: 5898 Free Union RoadFree Union, VA 22940

Monticello wineries, vineyards and cideries in Virginia.

Nestled in the middle of the picturesque Blue Ridge Mountains, Pippin Hill Farm & Vineyards offers the ultimate experience for those looking for farm to table food paired with award-winning wine. With almost 90 tons of grapes, including ten different varieties, grown on the property, Pippin Hill has its own signature Sauvignon Blancs, crisp Blanc de Blancs, Chardonnays, Cabernet Francs, and more. To spotlight local producers, Pippin Hill hosts Featured Farmer Fridays, a mini-farmers market that highlights the produce of local farmers. Visit Pippin Hill as a stop on the Monticello Wine Trail or book your own private event. 

Pippin Hill Farm & Vineyard Address: 5022 Plank Road, North Garden, VA 22959

Producing wine since 1990, the Thatch Winery is uniquely named for the roof on the building where the wine is made. Thatch Winery is the only winery in the United States with a custom, hand-crafted, thatched roof made from imported Turkish water reed. 

Located on 60 acres in Charlottesville, Virginia, visitors get to step back in time while experiencing the newly renovated tasting room and loft. As a maker of over a dozen wines, Thatch produces a wide variety, and each wine has a distinctive balance and complexity. Enjoy Thatch’s wines anywhere on the property including the gardens, patios, a terraced deck, two fireplaces, and three tasting bars. 

Open daily for tastings and tasty bites, on a behind the scenes vineyard tour, taste six specially curated wines, learn about the winemaking process from vine to bottle, and check out the barrel room. Since reservations are required and there is a four-person minimum, book early and bring a few friends.

View this post on Instagram We hope you're able to enjoy a full glass later on this fine Friday!?? And if you need to restock, we'll be here for curbside pickup from 12-4 both Saturday & Sunday! ?? ⁣ ⁣ Pre-ordering is not necessary, but always helpful ? Just call 434-760-4250 to place your order. A post shared by Thatch Winery (@thatchwinery) on Apr 17, 2020 at 8:18am PDT

Thatch Winery Address: 1650 Harris Creek Road, Charlottesville, VA 22902

Just a few miles from James Monroe’s Highland, Trump Winery sits on a stunning 1,300 acre lot. It’s the largest vineyard in Virginia. Some folks say the Trump Winery is magical and hosts the most memorable events. Their wine has won numerous national and international medals. The best part is, you can spend the day enjoying the wine, and then sleep the night away at their boutique luxury hotel, Albemarle Estate at Trump Winery . 

A stay at the Albemarle Estate is a must. Some have called it “one of America’s true treasures.” This 26,000 square foot, 45-room mansion, offers guests a night of elegance. There are ten luxurious guest rooms, each with detailed decor including twenty-foot hand-carved plaster ceilings, antique English rococo mantels, hand-painted wallpaper, crystal chandeliers, and more. 

The Trump Winery offers gourmet cuisine and breathtaking views of the vineyard. If you try the wines at Trump Winery once, you might become a regular.

When planning a trip to Richmond, use Hotel Planner  to help you find affordable and discounted hotels nearby. Create the perfect itinerary for your upcoming trip to the capital city and beyond with insightful tips and sample itineraries. Hotel Planner also shares average nightly rates by star rating. Hotels are even categorized by “luxury” and “affordable” groups. Each features notes about the property’s amenities including proximity to the airport and complimentary coffee. As you plan a trip to Richmond and neighboring Monticello Wine Trail, the birthplace of American wine, read the guest reviews to make sure that you’re picking the right accommodation for your travel style.

Monticello Wine Trail in Charlottesville, Virginia.

Brewery Wish List: Visit Three Breweries In St. Louis

Sip and Learn at the Irish Whiskey Museum in Dublin

Traditional Austrian Foods to Try in South Styria

monticello wine trail tour

Danielle Desir Corbett paid off $63,000 of student loan debt in 4 years, bought a house at 27, and has traveled to 27 countries, including her favorites, Iceland, China, and Bermuda. Go here to learn Danielle’s incredible story, from struggling financially and in debt to finding creative ways to earn more and live on her terms. Listen to The Thought Card Podcast , where Danielle shares how you can creatively travel more and build wealth regardless of your current financial situation. Reach out to Danielle by contacting: thethoughtcard (at) gmail (dot) com.

” I would like to invite you to join this website Sagatoto “

An amazing article to read. Thanks a lot for sharing this. Fine work. Keep it up.

Great Pictures! Thanks for sharing :)

Leave a Reply

Leave a reply cancel reply.

Your email address will not be published. Required fields are marked *

Wine With Our Family.png

  • Oct 30, 2022

Our Guide to Visiting the Monticello Wine Trail

Visiting the Monticello Wine Trail

The Charlottesville, Virginia region is known for its great wines. But with about 40 wineries spread out in different directions all around the city, how to tackle Charlottesville wine country, sometimes also known as the Monticello Wine Trail, depends on how much time you’re spending there.

While we have shared some of our favorite wineries across both Charlottesville and Central Virginia in previous posts, this is our guide to visiting the Monticello Wine Trail, an active association of wineries, all within 25 miles of Charlottesville, Virginia . We can personally attest to these places and their wines, as these are some of our favorite wineries to stop by when we’re in the area. But I admit this is a representative sample; we couldn’t list every single winery. If we didn’t mention one, that does not mean that you should avoid it.

Background of Charlottesville, Virginia Wine Country

This wine region is known by many as the birthplace of American wine , as it’s where President Thomas Jefferson first attempted to make wine back in 1807 . While his initial efforts failed, others took up the mantle, and the wine region grew, with many winemakers making impressive strides from the 1970s to today. The Monticello American Viticultural Area comprises one-third of Virginia’s vineyard acres and produces some of the best wine in Virginia. Many of these wines have won national and international acclaim.

If You Have Only One Day for Visiting the Monticello Wine Trail: Go South to the Wineries on Carter Mountain

Visiting the Monticello Wine Trail

Some of the wineries in Charlottesville’s Wine Country are just a few miles south of Charlottesville’s downtown area, on or near Carter Mountain. This mountain is also where you’ll find Monticello, Thomas Jefferson’s historic home, and Highland, President James Monroe’s estate. At some of these wineries you’re sampling wine while surrounded by lush forest.

A few of our favorite wineries in this area include tiny Gabriele Rausse Winery , Michael Shaps Wineworks , Jefferson Vineyards , and Blenheim Vineyards , which is owned by musician Dave Matthews of the Dave Matthews Band.

If You Have a Couple of Days for Visiting the Monticello Wine Trail: Venture Northwest Toward the Blue Ridge Mountains

Visiting the Monticello Wine Trail

About 30 minutes northwest of Charlottesville is a cluster of wineries at the foot of the Blue Ridge, where you can enjoy stunning views of the hills.

Some of our go-to wineries in this part of Charlottesville Wine Country include exotic-looking Glass House Winery , King Family Vineyards , Pollak Vineyards , and S tinson Vineyards (look out for the chickens).

If You Have One More Day: Go Northeast to Orange County

The towns of Gordonsville and Barboursville in Orange County, around 30 minutes northeast of Charlottesville, are home to several wineries. We tend to visit these wineries on our way to or from Charlottesville. The wineries in this region include the well-known Barboursville Vineyards , as well as Reynard Florence Winery and Honeh Lee Vineyard .

Visiting the Monticello Wine Trail

If You Can Squeeze it in: Go Further West to the Nelson 151 Route

A little further west of Charlottesville, closer to the Blue Ridge Mountains and the Appalachian Trail, are several wineries, cideries, distilleries, and breweries along Route 151 in Nelson County , which calls itself “Virginia’s Long Weekend Address.”

When we’re on this part of the Monticello Wine Trail some of our favorite places are Afton Mountain Vineyards (the lake is particularly pretty), Veritas Vineyards and Winery , and the smaller Flying Fox Vineyard and Winery .

Visiting the Monticello Wine Trail

While not officially a part of the Monticello Wine Trail, the region also hosts a number of other interesting places to grab a drink. To switch it up, we recommend Bold Rock Nellysford Cidery, featuring a variety of dry, sweet, and seasonal ciders, as well as Blue Mountain Brewery , with an ever-changing menu of beers and an option to try a flight of 10 (that’s not a typo!)

We hope our guide to visiting the Monticello Wine Trail will be helpful as you plan your next trip to the region. Please let us know if you have suggestions on what other wineries we should add to this list. Our email is [email protected] .

For more articles, visit our website and take a look at some of our related posts:

How to Prioritize a Visit to the Wineries in Fauquier County, Virginia

Three Central Virginia Wineries Worth a Detour

  • General Tips

Recent Posts

Three Great Winery Experiences in the Northern Rhone Valley

Why the New Study on Caffeine, Alcohol, and Sleep Deserves a Second Look

Our Wonderful Day Trip to the Wineries of Beaujolais

Your browser is not supported for this experience. We recommend using Chrome, Firefox, Edge, or Safari.


visitors guide


Sign up for our



  • 434-270-8839

5 Must-Visit Wineries on the Monticello Wine Trail

The sun is setting over the Blue Ridge Mountains; you’re holding onto a glass of some of the best American-made Viognier, and there’s relaxing live music serenading the chill atmosphere. This is every wine aficionado’s ideal moment. And it’s possible by taking a trip down the famed Monticello Wine Trail in Charlottesville, Virginia – aka., “The Birthplace of American Wine.”

The Monticello Wine Trail is a network of over 35 wineries around Charlottesville. The trail pays homage to the vision of one of America’s Founding Fathers, Thomas Jefferson. While living in Monticello, he dreamed of positioning Virginia as a hub for the best American wine—a dream realized after his lifetime thanks to the Monticello Wine Trail.

Whether you’re passing by C-Ville (dubbed the “Hook” for its ability to, well…hook you to its offerings) or you plan to relocate to the beautiful city, make sure you pay a visit to the following wineries on the Monticello Wine Trail.

Cunningham Creek Winery (CCW)

monticello wine trail tour

Located 10 minutes from Charlottesville, the Cunningham Creek Winery is arguably one of the best places to hang out with friends and family over a great selection of wine. As a family-owned business, CCW focuses on the nitty-gritty—from the finely crafted French wine varietals, friendly hosts, lovely setting to safety measures.

Cunningham Creek Winery is a relatively new winery, having opened its doors to enthusiastic tasters in 2016. But even in its infancy, oenophiles will appreciate the winery’s vinification expertise. (PS: Their 2017 Meritage & 2017 Estate Petit Verdot won the 2020 Virginia Governor’s Cup Gold Medals!) Based on online reviews by users, CCW is an ideal place for the family—including you’re four-legged friends (i.e., it’s a dog-friendly winery). 

They also host live music events in their expansive outdoor seating place, which offers good social distancing.

Tasting Price: Private tasting at $22 per person, including a private tour.

Address: 3304 Ruritan Lake Road, Palmyra, VA 22963 (Tel: 434-207-3907).

Jefferson Vineyards

monticello wine trail tour

If you’re a sucker for rich history like us, a visit to the Jefferson Vineyard is a must—and we bet you can already guess the reason why from the name of the estate! This is the exact location that Thomas Jefferson and Philip Mazzei (Italian winemaker) laid the groundwork to making Virginia the birthplace of American wine.

Jefferson Vineyards is owned and run by the Woodward family, which does an admirable job of honoring the Founding Father’s vision. It boasts a diverse portfolio of award-winning hand-crafted wines to excite your palate.

The estate is complimented by an awe-inspiring setting characterized by rolling hills and lush green forests. Pop up at the Jefferson Vineyards and sample some of their highly awarded Viognier. Chardonnay, Riesling, Rose, Cabernet Franc, or Petit Verdot.

Tasting Price: $12 per person for a classic tasting or $25 per person for a private tasting.

Address: 1353 Thomas Jefferson Parkway, Charlottesville, VA 22902 (Tel: 434-977-3042).

Veritas Vineyard and Winery

monticello wine trail tour

Veritas is arguably the most charming establishment on the Monticello Wine Trail. The family-owned estate’s seating areas are as cozy and homey as they get. There’s a relatively expansive lawn for the whole family (pups included), a huge picturesque tasting room, picnic table-style porch, a fireplace, and cozy couches, among other amenities that make the atmosphere welcoming.

Veritas offers a wide variety of wines—including an award-winning 2017 Petit Verdot, Viognier, Merlot, and Rose, to name a few. You can also sign up for site tours to experience every step of the captivating vinification process.

Tasting Price: $10 per person.

Address: 151 Veritas Lane, Afton, VA 22920 (Tel: 540-456-8000).

Pippin Hill Farm & Vineyard

monticello wine trail tour

Farm-to-table dining, anyone? Pippin Hill Farm and Vineyard is big on sustainable viticulture. The winery pairs their award-winning wines with ‘elevated cuisine’ – sourced from local farmers and their own Chef’s Garden. The Tasting Room menu highlights how the ingredients in your scrumptious meal were grown and harvested to take the dining experience up a notch.

The winery wins you over even before you enter the property. From the breathtaking view of the Monticello Wine Trail, grapes hanging from vineyards around the entrance, a pretty flowering hedge, to a spectacular patio dining area lined with bistro lights. And once you’re in, you get a chance to sample exquisite craft winemaking from the renowned Michael Shaps.

In a nutshell, Pippin Hill is the place to go for an all-around experience.

Address: 5022 Plank Road, North Garden, VA 22959 (Tel: 434-202-8063).

Barboursville Vineyards

monticello wine trail tour

Like the Jefferson Vineyards, Barboursville Vineyards is rich in history. It’s nestled on an 18th-century estate that was home to Virginia’s former Governor, James Barbour (1812-1814). For a walk down history lane, you can take a tour of the ruin of Governor Barbour’s old mansion—which so happens to be the architectural work of Thomas Jefferson.

Barboursville is also revered for its expansive wine tasting selection. There are around 20 wine tasting to appease your palate. But if you’re short on time, don’t miss out on their signature Octagon wine blend.

Tasting Price: $7 per person.

Address: 17655 Winery Road, Barboursville, VA 22923 (Tel: 540-832-3824).

Recent Posts

Top 6 Bathroom Design Trends for 2024

Top 6 Bathroom Design Trends for 2024

A Comprehensive Guide to the Home Buying Process

A Comprehensive Guide to the Home Buying Process

monticello wine trail tour

You want to sell your home. Let's discuss it.

Experience the stress-free way of selling your home, let’s discuss today!

* Other terms & conditions apply. Seller must enroll in the program prior to listing their home.

  • Sell Your Home
  • Buy Your Home
  • Meet the Team
  • Privacy Policy
  • 900 Gardens Blvd Suite 100, Charlottesville, Va 22901
  • © Copyright 2023, Avenue Realty, LLC. All Rights Reserved.

Sign In to Save Homes & Searches

Stay informed on price reductions, new homes that match your search & other insider information.

Monticello Wine Tour & Coach Co.

monticello wine trail tour

  • See all photos

monticello wine trail tour

Similar Experiences

monticello wine trail tour

Monticello Wine Tour & Coach Co. - All You Need to Know BEFORE You Go (with Photos)

Monticello wine tour & coach co. information.

Charlottesville Wine Tours


The Commonwealth of Virginia is the 5th largest producer of wine in the United States.

The monticello wine trail is virginia’s crown-jewel, truly fulfilling thomas jefferson’s vision of wine-making in virginia..

Norm’s Transportation offers a variety of tours to Charlottesville area wineries. You can choose and customize your tour from the wineries listed below OR pair a couple of wineries with a historic attraction if you’d like. We’ll take you there in style and get you back safe and sound! We typically use full or mid-sized SUVs, vans and sedans to accommodate up to 14 passengers.

NOTE: Due to their restrictions on groups, we highly recommend making reservations ahead of time. Norm’s Transportation’s tour pricing is for the group, not per person. All prices are based on Charlottesville being the starting/ending location. An extra charge for locations outside the general Charlottesville area may be applied. Below are short descriptions of our local wineries. Be sure to check out our list of planned tours or customize a tour of your own. Tip: You can mix and match wineries, breweries and historic venues!


Winery Tours List

King Family Vineyards offers great wine coupled with breathtaking vistas of the Blue Ridge Mountains, and a top-notch staff who understands hospitality. The vineyard is well known for its Meritage, a Bordeaux style blend of four red varietals. King Family offers a gourmet assortment of chocolates, cheeses, salamis, spreads, and hot French bread. Or you could bring a picnic.

Tip: King Family Vineyards hosts weekly polo matches, held on Sundays from Memorial Day through early October. Buy a bottle of wine at the tasting room and enjoy the game!

Mountain & Vine Vineyards & Winery: Relax in the serene, gorgeous natural landscape of DelFosse Vineyards while enjoying award-winning wines by the glass or the bottle. Surrounded by beautiful mountains and rows of picturesque grape vines, DelFosse Vineyards and Winery offers a stunning natural setting.

Hilltop Berry Farm and Winery specialize in wine made from fruit other than grapes. Their selection of handcrafted “True to the Fruit” wines and authentic honey meads offers a unique tasting experience, as well as the opportunity to taste fermented drinks originally enjoyed by ancient cultures from around the world.

Brent Manor Vineyards: Nestled in the hills of Virginia Wine Country in beautiful Nelson County just South of Charlottesville, The Brent Manor Vineyards welcomes you to a mix of the New World and the Old World. When you visit our tasting room, you get to experience our wines, and in addition, we are bringing the Old World in as well by offering an ever-changing variety of Portuguese wines.

Veritas Vineyard and Winery started as the family’s labor of love and has grown into one of the best event destinations in the region. Enjoy their popular wines and relax in the elegant tasting room, from the porch or on the lawn featuring breathtaking views. Pollak Vineyards offers a picturesque lake and dramatic views of the Blue Ridge Mountains. But it’s not just the setting that demands attention. Their wines have been widely recognized as some of the finest in the region.

Veritas offers a cheese plate of three kinds of gourmet cheese, homemade apple chutney, and warm baguette.

Afton Mountain Vineyards: If their slogan “grapes don’t grow in ugly places” is true, they have nothing to worry about: Afton Mountain Vineyards is surrounded by beautiful vistas. The beautiful setting, welcoming atmosphere and excellent wines make it a memorable stop on your tour.

Afton offers a selection of meats and cheeses. You are welcome to bring a picnic to enjoy along with the wine and mountain views.

Jefferson Vineyards realizes Thomas Jefferson’s dream of making fine Virginia wine. They still grow the majority of their fruit on sites selected by Jefferson in 1774. Their wines won several prizes and awards and some believe Jefferson’s Viognier is some of the finest this side of Condrieu.

Trump Winery is situated in the heart of the Monticello Wine Trail and features almost 1,300 acres of breathtaking scenery. Enjoy the view while sipping award-winning white, red, and sparkling wines. They also offer a regionally inspired menu of artisanal cheeses, gourmet pizzas, and rustic sandwiches.

Septenary Winery – Situated on 109 acres of rolling hills surrounded by the Blue Ridge Mountains, Seven Oaks Farm and Vineyards is a magnificent property located just 15 minutes from Charlottesville in Greenwood, VA.

Valley Road Vineyards – Founded in 2015, Valley Road Vineyards was conceived by a group of friends who brought talents from successful careers in law, advertising, insurance, real estate development, and writing, among others. With their mutual love of Virginia and wine, a vineyard operation in the heart of the Monticello Viticulture Area seemed a good choice for a fun and rewarding business venture. Led by co-founder and CEO Stan Joynes, the group found an ideal site for a new vineyard and tasting room on Rte 151 at the head of the Rockfish Valley in Afton, Virginia. The first vines were planted in the spring of 2016, and VRV bottled its first wines in April.

*Tour pricing is based on a 5-hour time frame. Additional time will be charged accordingly.

If you don't find what you're looking for here, call us! (434) 989-8905 or fill out the form below! We'll work with you to plan your ideal tour.

The Boutique Adventurer: Luxury Adventure Travel Blog focussed on Emerging Destinations for those over 35

15 Wineries in Charlottesville Va You’ll Love I Monticello Wine Trail

By: Author Amanda OBrien

Posted on Last updated: 28/03/2023

Did you know that Virginia has one of the most exciting and innovative wine scenes in the world today? I didn’t either until I visited lovely Charlottesville and its Monticello Wine Trail .

The first vines were brought to Virginia by Thomas Jefferson at the end of the 18th century. He had correctly identified the terroir of Charlottesville as being ideal for vineyards. Alas, he had not assessed the best grapes for the soil and climate of Charlottesville, and his attempts to start the Virginia wine industry failed.

For the next couple of hundred years, there was no wine industry in Charlottesville. An opportunity was created in the 1970s when state laws began to change, and there was new potential for wineries. In 1979 there were six wineries in Virginia. The number grew slowly to 50 in 2000; today there are more than 350. More than 40 of those are the wineries in Charlottesville VA, that comprise the Monticello Wine Trail.

Of course, there is more to Charlottesville than just wine. I will take you through 15 fantastic Charlottesville wineries (in no particular order) and then cover some other kinds of non-wine things to do. Plus I will cover where I ate, where I stayed etc etc. Before I get to the wineries, I want to run through the key grapes grown in Charlottesville.

jefferson vineyards charlottesville

  • Charlottesville Grapes

Table of Contents

Virginia Wine Competitions

15 fantastic wineries in charlottesville va, 1. michael shaps, 2. jefferson vineyards, 3. pippin hill farm and vineyard, 4. loving cup, 5. wisdom oak winery, 6. keswick vineyards, 7. gabriele rausse winery, 8. eastwood farm and winery, 9. blenheim vineyards, 10. king family vineyards, 11. stinson vineyards, 12. afton mountain vineyards, 13. barboursville vineyards, 14. veritas, 15. trump winery, how to plan your monticello wine trail visit, things to do in charlottesville that aren’t wine tasting (exactly), 1. cider tasting at albemarle ciderworks, 2. visit monticello, 3. visit the university of virginia, 4. farmers market at ix art park, 5. visit the wool factory, 6. carter mountain orchard, how to get to charlottesville, virginia, charlottesville restaurants, charlottesville boutique hotels, last word on charlottesville wineries.

Viognier is the major white grape grown in Charlottesville. Chardonnay also grows in the region as well as the less well-known Petit Manseng grape. Chardonnay tends to be grown more often in Northern Virginia as Charlottesville can be a bit warm.

Petit Manseng is a grape that lasts until quite late in the season and makes delicious dry white wines. Personally, I am a Chardonnay drinker and I loved the Petit Manseng wines I tried while on the Monticello Wine Trail. Viognier and Petit Manseng are the primary white grapes in Charlottesville.

pippin hill vines

Like Bordeaux , Charlottesville is all about blending its reds. The main red grape is Cabernet France and there is also some Cabernet Sauvignon. Petit Verdot is also grown. This grape is traditionally used for blends in Bordeaux, but in Virginia, it features as a single varietal. It produces a dark purple, full-bodied wine with bold tannins that age well. Petit Verdot is Virginia’s equivalent of the California Cabernet.

Finally, Virginia has a unique indigenous red grape known as the Norton, which can be quite polarising. It’s a deep purple grape with flavors of dark fruits and a rich, fruity aroma.

Virginia takes its wine competitions very seriously. All of the wineries that I visited were proud to mention the positions they had achieved in the competitions held throughout the state. The biggest wine competition in Virginia is the Governor’s Cup. This state wine competition is held every year, and the wineries of Monticello tend to take home more than half of the gold medals each year.

The Governor’s Cup produces what is known as the Governor’s Case. These 12 wines are then declared to be the best in the state of Virginia. It is a major honor to be included in the Governor’s Case.

The local version of the Governor’s Cup is the Monticello Cup. Entry criteria include being a member of the Monticello Wine Trail and the wine must contain at least 85% fruit from the Monticello AVA.

Michael Shaps is one of the best-known names in the Virginia wine industry. Shaps studied winemaking in France and arrived in Virginia in 1995 when the industry consisted of 45 wineries. He began his career at Jefferson Vineyards and then started his own vineyards as well as a consulting business in 2007.

michael shaps wineworks wineries in charlottesville va

Shaps also started his own vineyard in Mersault, Burgundy in 2004. Today Maison Shaps is run by his oldest daughter.

It was Shaps who championed the Petit Manseng grape in Virginia. This high-acid white grape was originally used for sweet wines. However, in 2012 Michael began making a dry wine from Petit Manseng and aged it in French Oak barrels. Today, Petit Manseng and Viognier are his two most popular sellers.

shaps tasting room

Michael’s Petit Manseng was one of the first wines I tried in Charlottesville, and I absolutely loved it. I bought a bottle to take home. I drank it with a friend nearly two months later, and it tasted even better than I remembered.

Michael is quite experimental when it comes to sparkling wines. His Blanc de Franc uses cabernet franc grapes rather than pinot noir, and he also has a sparkling made with Riesling. Both are made using the traditional method.

michael shaps wine

Don’t leave without trying Michael’s dessert wines. Michael uses old tobacco curing barns to dehydrate grapes he uses to make dessert wine. He makes a petit manseng dessert wine (Raisin d’etre) as well as a cabernet franc version.

The Michael Shaps Winery is about 10 miles outside of Charlottesville. However, Michael has also set up a tasting room/wine bar called Michael Shaps Wineworks Extended in Charlottesville. Wineworks Extended features the same wines you would taste at the main winery as well as some extra listings.

michael shaps shop

Michael also owns a vineyard in France and it is possible to try those wines as well as some of his personal favourites. Try a flight of Michael’s French Wines or Virginia Wines for just USD$10 each or enjoy the wine on tap.

Michael Shaps Wineworks Extended is open between 1pm and 7pm for wine and snacks. The main winery is open daily from 11am to 5pm.

This family owned and run winery is perhaps the best known winery in Charottesville – the name and history of course help! (more of that to come). But don’t let the well known name put you off – Jefferson Vineyards was one of my favourite wineries in Charlottesville VA and I came home with a few bottles.

jefferson vineyards glass of wine

Let’s start with the location of Jefferson Vineyards. It is just 10 minutes from Charlottesville and a stone’s throw from Monticello. You’ll know you’ve arrived when you see the extremely picturesque St Luke’s Episcopal Church and some beautiful vineyards.

Thomas Jefferson and Phillip Mazzei began growing grapes on the Jefferson Vineyards estate almost 250 years ago. Jefferson brought Chianti viticulturists over from Italy to assist in planting and growing grapes. This is why all Jefferson Vineyards bottles bear the signature of Jefferson.

jefferson vineyards

Alas, none of those vines exists today, but the history of the land inspired Stanley and Shirley Woodward to begin growing grapes again on the land in 1981. With the assistance of the father of the Virginia wine industry, Gabriele Rausse, the winery began to flourish. Today, the winery is managed by their grandchildren, Attila and Alexa Woodward.

Jefferson Vineyards Manager and Winemaker

The winery is best known for its Bordeaux style blends, Viognier and Petit Verdot. Jefferson was the first winery in Charlottesville to make a single varietal Petit Verdot. Winemaker Chris Ritzcovan stores the Viognier in a mix of French and Hungarian oak barrels as well as a little stainless steel to reduce the grape’s natural acidity and provide a soft mouth feel and longer finish.

jefferson vineyards

There are two tasting rooms at the winery itself but I would recommend taking your wine outside to enjoy the vineyard’s beautiful patios and their stunning views. Jefferson has four tiers of wine from table to reserve and there are usually two seasonal wine flights that each feature four wines. Wine is also sold by the glass or bottle.

The Jefferson Vineyards tasting room is open Wednesday through Sunday 11am to 6pm and they also serve cheese and charcuterie.

The beautiful Pippin Hill has a wonderful location on top of a hill with sweeping views across their vineyards and the local area. The vineyard also has as beautiful gardens. No wonder it is a popular spot for weddings.

pippin hill

Pippin Hill is also known for its excellent restaurant that features many ingredients from the gardens on site. I combined a lovely lunch at Pippin Hill with my wine tasting and highly recommend this option.

pippin hill charlottesville winery

Pippin Hill works closely with Michael Shaps to produce sauvignon blanc, barrel fermented Chardonnay, Blanc de Blanc and Cabernet Franc. It also produces other varietals but it is these wines for which it is best known.

pippin hill wine flight

I enjoyed a tableside white wine flight tasting with my meal. Small apothecary style bottles became popular for wine flights in the area during covid and have been kept on – they are so cute! My flight included Pippin Hill’s zero white blend, chardonnay, petit manseng and rose. There is, of course, also a red wine table flight option.

pippin hill hummous

The menu is a mix of items designed for sharing like boards and salads and small plates. It changes seasonally. The winery has a buzzing tasting room with a high ceiling inside. Restaurant tables are mostly outside. Estate tastings are also available which include a tour of the estate, a wine tasting and food. These can be booked for groups sizes up to 10.

pippin hill tasting room

The tasting room at Pippin Hill is open most days with different levels of food available. The winery also hosts events like live music and cooking classes. All events, tastings, meals etc can be booked on the Pippin Hill website.

pippin hill glass

Loving Cup is the only certified organic vineyard and winery in Virginia and has been so for ten years. It’s a very relaxed and comfortable winery with lots of outdoor seating. Loving Cup offers wine flights as well as bottles and glasses of wine.

Loving Cup winery sign

I was able to see the actual winery but alas it wasn’t open when I visited (they are only open Friday to Sunday). I heard good things about their wines so check it out and send me an email.

The winery is located at the end of a rather long windy gravel road – there are reassuring signs along the way!

Wisdom Oak is one of the hottest wineries in town after winning the Monticello Cup and being included in the Governor’s Case in the same year. This would be a major achievement for any winemaker on the Monticello Trail. However, when you learn the story of Wisdom Oak Winery it becomes even more impressive.

wisdom oak winemaker

Jason and Laura Lavallee lived the corporate life in Philadelphia . When they acquired their gorgeous dogs they realised they couldn’t travel as frequently. They were both mad about wine but had no training.

In 2015 they bought 126 acres of run down winery with just 800 vines and started farming it. The first vintage was in 2016 and the awards started coming in 2018. Jason will be the first to say that the support of the very collaborative and kind local wine industry was instrumental to the winery’s success.

wisdom oak winery

The vineyard is named after one big beautiful tree on its land – the Wisdom Oak. Their Petit Verdot is the wine in the Governor’s Case (I took a bottle of this home – it is quite fantastic) and their 19 Bordeaux style blend was the winner of the Monticello Cup. And don’t miss their fantastic Petit Manseng.

wisdom oak vines charlottesville wineries

Jason loves to experiment and does many small productions of different types of wines. Wisdom Oak has a wine club that plays a big part in vetting these experimental wines. Unlike their European counterparts, winemakers in Virginia have considerable flexibility in developing new varietals and blends.

Wisdom Oak also produces Albariño, which isn’t a common varietal in Virginia, as well as a successful port. They were working on their traditional method sparkling when I visited – I am keen to taste the results.

wisdom oak glass

The tasting room at Wisdom Oak Winery is open Thursday to Sunday. There is plenty of outdoor seating and space to lay down a rug and enjoy the vines. Seasonal food items are often available on the weekend.

Stephen Barnard is one of Virginia’s best known winemakers. Originally from South Africa, he has been making wine for 20 years and is the winemaker at family owned Keswick Vineyards .

Keswick Vineyard’s first vintage was in 2002. Their focus is on high acid wines that pair well with food. Stephen looks to maximise the value of their clay based soil which slows down the ripening of the fruit. Barnard is a big fan of acidity for three reasons.

keswick winery

Firstly, wines with higher acidity tend to pair better with food and secondly higher acid often results in lower alcohol levels which are becoming more popular amongst his audience. The third benefit of higher acid levels is less need for preservatives allowing for a more natural wine.

Stephen tends to focus on single varietals much more than blends. They are known for their Viognier and they make a lighter, citrus flavoured Chardonnay with no oak. I was a big fan of their reds, particularly the Cabernet and Petit Verdot. They also make a Cabernet Franc, rose and several other varietals.

keswick winery

Keswick also has two wine clubs. The “standard” wine club involves regular wine shipments, tastings, discounts etc. They also have the Barrel Owner’s Club that allows members to own their own barrels and of course the wine inside.

Like all the wineries in Charlottesville VA I visited, Keswick is very well set up for tastings both inside and outside. Wine flights can be custom built and Stephen likes to visit so you may well meet him too!

Gabriele Rausse is known as the father of the Virginia wine industry. He arrived in Virginia in 1976 from his native Italy. In 1977 he began grafting vines in a manner he thought suited the local environment and for the first time in the Virginia wine industry 99% of the vines survived.

gabriele rousseau

Rausse made his first wines in 1978 under the Barboursville brand. His PhD in plant pathology and upbringing in the Veneto region of Italy convinced him that there could be a Virginia wine industry – despite being told by virtually everyone he met that this was not possible.

By 1981, Rausse had started providing consultancy to the new winemakers in the industry and he also moved to Jefferson Vineyards where he was the winemaker for some time. In 1995 he took a job at Monticello as the assistant director of their beautiful gardens.

I was lucky enough to meet Gabriele at Monticello. In addition to looking after their rather large gardens he continues to consult and has his own winery.

When I asked Rausse what he thought made Virginia wine unique his response was “it’s all about the soil” as many winemakers will say. However, he did add that vines like temperature variation and Virginia have a lot of that! These two elements combined create the base for what makes Virginia wines different.

gabriele rousseau winery

Rausse’s winery feels like walking into someone’s beautiful home in the Swiss mountains. There are lots of windows, lots of oak and a very relaxed feel. If you like rose don’t miss visiting the Gabriele Rausse Winery . I was told by multiple people that I needed to try his sparkling rose and it was fantastic. Plus, Rausse loves to experiment and there are loads of interesting rose variants available for tasting.

gabriele rousseau tasting room

Rausse sources grapes from a range of vineyards and make many unique wines for the region such as Malvasia and orange wines. His reds are quite light in texture and he often uses Nebbiolo grapes.

The Rausse winery is the perfect place to relax for an afternoon of wine tasting, particularly if you like to try innovative experimental wines (he also has the classics).

The winery is open for tastings on Thursdays, Fridays and Sundays.

gabrielle rousseau tasting flight

NB: The winery doesn’t appear to have a sign so it isn’t easy to find. If you hit the Trump Winery you’ve gone too far.

I am always very pleased to meet another female entrepreneur and Athena Eastwood was a delight. A former commodities trader, she purchased the land around what is now Eastwood Farm and Winery in 2016.

eastwood winery charlottesville

Eastwood is a different kind of winery. Eastwood doesn’t have their own vineyard. Instead they source from and invest in different growers in the area under a partnership model. They are very community focussed and work closely with charities in the area. And if you’re travelling with kids this is the winery to visit as it is designed to be family (and dog) friendly.

eastwood winery tasting

Eastwood opened at the end of 2020 and the tasting barn opened in February 2021. All of their white wines have won silver at the Governor’s Cup. They have a stainless steel stored Chardonnay that is fantastic if you like your Chardonnay a bit more acidic with a strong green apple flavour.

eastwood winery tasting room

If you prefer a softer chardonnay try their reserve. It is oak aged for 20 months and doesn’t have the buttery burst of a California chardonnay. Instead, you’ll enjoy honeysuckle and apricot on the palate – my kind of wine!

eastwood winery flatbread

On the red side, the Eastwood Merlot is soft and low on tannins so very drinkable. Their cabernet franc has a great nose and gives lots of cherry on the palate. Their meritage is a blend which is heavy on cabernet sauvignon and goes back into oak for 12 months after it has been blended. This is their Bordeaux style blend and if you like your reds big and deep this is for you.

eastwood winery bottles

Athena is a single mum with three kids and a grandchild so Eastwood also offers juice flights for kids! And she keeps the tasting room open till 8pm in the evenings so locals can visit after work. The tasting room is open Wednesday to Sunday.

Dave Matthews bought his mother a house outside Charlottesville in the 1990s. When he learnt of the wine potential (and history) of the area he decided he wanted to explore the opportunity and appointed his brother to manage the project.

blenheim winery tasting room

They developed four “blocks” of vineyards in 2000 and have now been producing sustainable Virginia wines for 10 years. Over that time Blenheim Vineyards has only had two winemakers and I was fortunate enough to spend some time with their current winemaker, Kirsty Harmon.

Kirsty wanted to be a scientist until she met Gabriele Rausse (his name pops up everywhere!). He convinced her to become a winemaker and she travelled through California, France and New Zealand to learn her trade.

blenheim winery bottle

At Blenheim, her style is to produce high acidity approachable wines that go well with everyday foods. Her wines are lighter in style and tend to be lower in alcohol. No wine is kept in a barrel at Blenheim for more than 12 months. They have 17 different grape varietals planted across the estate and Dave Matthews designs the wine’s modern graphic labels.

blenheim winery vines

Blenheim offers a one hour guided tasting for $25 or you can enjoy a glass or a flight if the guided tastings are full. The vineyard has lots of lovely outdoor space that is perfect for wine tasting. The tasting room is open Thursday through Mondays.

I visited King Family Vineyards on my final day in Charlottesville. Throughout my trip I was asked multiple times if I was visiting Kings so my expectations were high. I am glad to say that they were exceeded!

The vineyard is located in the Crozet area which was once the peach capital of the world. The King family (mum and dad and three sons) left Houston in 1995 and were seeking a farm where they could also play polo. When they first moved in they learnt that their new farm had the potential to produce some great grapes and they were hooked.

king family charlottesville wineries

They sold their first bottle of wine in 2000. They have grown from eight to forty-eight acres over that time and will produce 22,000 cases in 2023. And all three sons and their families work in the business and live nearby.

king family winery charlottesville

King Family Vineyards are known for having some of the best quality approachable wines in Virginia. This was my favourite viognier of the trip – fruity yet soft the acidity was perfectly balanced. Their chardonnay is made in the burgundy style so it is fruiter and light on the oak.

king family winery red wine

The King Family reds were my personal favourites. I love jammy black fruits and heavy body in my reds so the Petit Verdot was a big hit.

The polo field opened in 2004 and an average match these days has 2500 attendees. Plus they hold over 100 weddings each year – it is easy to see why when visiting the beautiful King Family estate. And they have a wine club.

king family winery outdoor area

Wine tastings are offered daily between 10am and 5pm. Self guided flights are available in a classic or seasonal theme. For a little extra enjoy five wines and a guide or try six wines in the lovely King Family library for a little more again.

This family run vineyard specialises in small lot wines. Stinson is run by a father/daughter team and her husband. The winery is located in what was a three car garage. The family are big fans of French wine and use traditional french wine making techniques such as whole berry fermentation for their red wines.

stinson vineyard

Stinson’s most popular wine is their 100% merlot Rose called Crose. The second best seller is their Meritage which featured in the most recent Governor’s Case.

stinson vineyard

The tasting room is open Thursday through Sunday and visitors can enjoy wine flights or grab a bottle or glass. There is a lovely large garden area with comfortable seating. Plus they have a lovely bed and breakfast next door if you feel like staying the night!

Afton Mountain Vineyards sits at the western end of the Monticello Wine Trail and has some spectacular views over the countryside. I was able to have a quick look around Afton but alas I didn’t have time to stay for a tasting. I deeply regretted this as it was so relaxed with lots of comfortable outdoor seating.

afton mountain

Grapes were first planted on this farm in 1978 so it is one of the older wine farms. The site was acquired by its current owners in 2009.

Afton Mountain Vineyards is open Thursday to Sunday between 11 and 5 for tastings. Wine flights are on offer as are wines by the glass and bottle.

afton mountain (2)

Barboursville Vineyards is one of the oldest wineries on the Monticello Trail. Run by three Italian brothers it came up frequently during my trip as one of the best Charlottesville wineries to visit. Alas, I wasn’t able to visit but don’t let that stop you – and do email me if you do and let me know your thoughts.

Their tasting room is open every day.

Veritas is owned by an English couple, Andrew and Patricia. Their first vintage was in 2001. This is very much a family winery as all three of their children also work for the business. I didn’t have time to do a tasting but I did drive through their beautiful property.

veritas vineyards

Veritas offers two wine flights for tasting – a classic and a reserve. They are open for tastings every day and also have a bed and breakfast, The Farmhouse.

Trump Winery is actually the largest Charlottesville winery so I thought I better put them on the list. I didn’t get a chance to visit but it is a very successful winery.

The Monticello Wine Trail is made up of more than 30 wineries, all of which are in within 25 miles of Charlottesville. The easiest way to visit wineries is of course to drive. However, this does mean that someone has to be the driver and can’t swallow the wine.

Many of the wineries are so close to Charlottesville that it would be possible to take a uber taxi there and back as well as potentially inbetween (few are walking distance from each other due to the size of most vineyards). Do note that cell signals can be patchy in some areas of the Monticello Wine Trail.

Another option is to hire a driver for the day. The Charlottesville tourism office has quite a few links to different types of drivers .

Hop on Cville organises winery tours which cover sub-regions of the area. The Croze t Trolley offers winery tours on Friday evenings. Vin Go Tours offers private wine tours.

For most of the available options, it will be necessary to have a sense of where you would like to visit. If you like the sound of the wineries I visited in this article I would suggest the following to ensure you spend more time tasting than in the car:

  • Combine the wineries closest to Monticello – Jefferson Vineyards, Gabriele Rausse Vineyards, Blenheim Vineyards, Wisdom Oak Winery, Pippin Hill
  • Combine the wineries near Crozet – King Family Vineyards, Stinson Vineyards, Afton Mountain Vineyards, Veritas Vineyards

And no matter what option you choose don’t miss an evening visit to Michael Shaps Wineworks Extended. It is actually in Charlottesville and walkable from the city centre.

Albemarle began as a cidery in 2009. Prior to that, it was an apple farm without the cider. The farm grows over 200 different varieties of apples. What I found most interesting about Albermarle Ciderworks is that they approach cider like wine in that they make single varietal ciders as well as cider blends.

albemarle bottles

Albemarle makes cider in a process that resembles winemaking. Yeast is added to the juice and they generally don’t add any sugar. This results in dryer cider with alcohol levels between 7 and 10%.

Albemarle’s signature apple is the pippin and their Royal Pippin cider has a wonderfully clean, fresh taste. It is made from 100% Albemarle pippin apples. Their Jupiter’s Legacy cider contains a blend of between 20 to 30 apple varieties for a dry, smooth cider experience.


If you’re after a slightly sweeter cider try the Virginia Hewes Crab. If that isn’t sweet enough try Albemarle’s best selling Pomme Mary, their sweetest cider of all.

The latest from Albemarle is Harrison. Harrison cider is made with dabanatt apples which are more european in style and contain some tannins.

The Albemarle Ciderworks tasting room is open Wednesday through Sunday 11-5.

albemarle glass

You can’t go to Charlottesville and not visit Monticello, the former home of Thomas Jefferson and the building on the back of the US 5 cent coin or nickel. Monticello means little mountain in Italian. Monticello was Jefferson’s home from 1770 until he died in 1826.


Today Monticello is a UNESCO site. It is the only house in the United States to receive a UNESCO World Heritage Site designation.

When you arrive at Monticello, park at the visitor’s centre. Arrive at least 30 minutes prior to your scheduled tour as it is necessary to take a shuttle bus from the visitor’s centre up to Monticello itself. Most tickets include a guided tour of inside Monticello.


After the tour, it is possible to explore the beautiful grounds. The West Garden provides the view that can be seen on the nickel coin. There are also guided tours of the grounds available as well as tours that delve into more detail about slavery and the property. Finally, don’t miss seeing Thomas Jefferson himself. An actor who plays Thomas Jefferson regularly pontificates by the pond.

Monticello is open most days but that can vary across the seasons so do check their website. Same day tickets can be purchased at Monticello but to avoid disappointment I would suggest booking online ahead of your visit.

Thomas Jefferson also designed the University of Virginia – he was a busy man! The university was founded in 1819 and the beautiful Rotunda is the signature building on campus. It is on the lawn outside the Rotunda that graduation ceremonies are held. A lucky few receive one of the dorm rooms which borders the lawn.

university of virginia

The Rotunda building itself is open to all and free to visit. There are areas for studying as well as spaces to hold meetings. Jefferson envisaged this to be the hub of the University. The gardens behind the rotunda are lovely and are also free to visit.

university of virginia rotunda

In April of 2020 a beautiful water memorial was opened in a tribute to the enslaved labourers at the university. Key events in the history of the University as well as facts about the use of enslaved labourers are engraved into the fountain.

university of virginia fountain

IX is 24 hour free mural and sculpture art park in Charlottesville. It was created to allow locals to celebrate their creativity and to encourage community collaborations. It is home to Virginia’s first immersive art exhibit, The Looking Glass, and every Saturday almost 60 local vendors participate in the IX Art Park Farmers Market.

charlottesville market

This lovely space is home to several small businesses working together. Selvedge Brewing is a craft brewer and has a great casual restaurant. For a more upmarket dining experience head to Broadcloth. The Workshop offers coffee and wine all day long.

wool factory

The Wool Factory has also worked with a local winemaker to develop a range of Virginia wines. I was particularly impressed by their sparkling wine which was developed by a French winemaker using the traditional method. It is made from 100% Virginia chardonnay grapes. The range also includes a petit manseng and a cabernet franc.

wool factory wines

The Wool Factory is the perfect place to come and sample Virginia wine. In addition to their own wines, The Workshop also sells many other local wines that can be purchased and then drunk in the lovely big outdoor area. They also offer an ever changing selection of wines by the glass.

wool factory wines for sale

I had a wonderful dinner from Selvedge and sat outside enjoying local wine and the great atmosphere at The Wool Factory.

Carter Mountain Orchard offer pick your own fruit opportunities, concerts, a giant Country Store filled with some fantastic home made treats and one of the best views in Charlottesville all year round. It is deservedly famous for its delicious apple cider donuts.

carter mountain orchard

There is a wine shop and a cider cellar that both offer tastings and retail. There is plenty of outdoor space so it is simple to buy a bottle of something, grab some glasses and sit down and enjoy the amazing views.

carter mountain orchard

If you’re travelling from overseas the closest International airport is Washington DC Dulles International.

If you’re travelling from within the United States , Charlottesville airport has good connections with several major US airport hubs. Amtrak train routes also run through Charlottesville and connect with many of the main metropolitan areas on the East Coast.

The centre of Charlottesville, particularly the pedestrianised area, is very walkable.

I enjoyed everything I ate and drank in Charlottesville but I had two particular favourites. The first was Crush Pad . This wine bar/shop has a prime position on main street and offers a huge selection of wines to buy or taste plus some fantastic small plates and boards.

Crush Pad wine bar charlottesville

Crush Pad was set up by local wine expert Vincent Derquenne and the bar has such a friendly and warm feel. I arrived on my own and Vincent immediately struck up a conversation. I felt so at home sitting there trying different wines. I liked it so much that I went twice during my visit to Charlottesville.

My other favourite spot in Charlottesville was the bakery/cafe Petite Mariebette . This charming cafe is stocked with delicious french pastries as well as a fantastic brunch menu. The French blue counter offsets a light airy slightly industrial feeling design aesthetic and it all comes together to make for a very comfortable environment you won’t want to leave.

petite mariebette

The coffee is fantastic – and I am very picky about my coffee – and every coffee comes with a delicious canele. On my first visit, I went savoury and had a breakfast bowl with an egg, avocado, fetta cheese, spinach, lentils and red onions. I tried the parfait on visit two with fantastic yoghurt and granola.

petite mariebette breakfast

Public Fish and Oyster is a super friendly relaxed restaurant featuring well fish and oysters! There is a huge range of oysters available – I just asked them to choose a mix for me – all with their delicious cocktail sauce. Next up was grilled fish on Mediterranean grilled vegetables. Seating is both inside and outside.

Public oysters

The Dairy market has a mix of interesting food vendors under one roof. Chose from Mexican, pizza , Japanese, Latin American and more. I had a great dinner at the Milkman with some very tasty tuna tartare and an avocado salad that was served on half a lettuce.

Dairy Market

If you’re looking for a restaurant with atmosphere and live music head to The Whiskey Jar on main street. Most items on the classic Southern food menu are locally sourced and the menu changes seasonally. I was a little dull and went with a classic hamburger which was delicious. Best of all I enjoyed my burger listening to some great live music.

whiskey jar

The Local features a modern American menu that is also heavy on local sourcing. It offers a mix of american classics like caesar salad, crispy shrimp, meatloaf and pasta dishes. I enjoyed some lovely grilled salmon and couldn’t resist ordering the worth-every-calorie Brownie sundae.

The Local Charlottesville

If you’re hungry when you visit Monticello pop into Michie Tavern . This old time style restaurant features a buffet/cafeteria set up with chicken (fried, roasted or pulled), biscuits, black eyed peas, beetroot, mashed potato and coleslaw. Help yourself to the buffet the first time and then the staff take care of 2nds, 3rds etc and dessert.

michie tavern

For some more delicious pastries head to the Albermarle bakery – great cinnamon buns!

albemarle cinnamon bun

I was lucky enough to stay in two boutique hotels during my stay in Charlottesville. The first was The Jeff Hotel. The Jeff has a fantastic location literally on the main pedestrianised street in downtown Charlottesville.

jeff hotel

The Jeff is a self service hotel. This means customers receive a check in code by email before arriving. The check in code is then used to open the main entrance (on the pedestrian strip) as well as the individual room. So it feels more like an apartment than a hotel which is exactly the point. The Jeff is about allowing visitors to live like a local.

jeff hotel living room

The rooms themselves are light and bright and feature a nordic style color pallet with some nice luxurious touches. My suite had a comfortable sitting room with a big suede couch as well as a large bedroom with a custom made very comfortable king sized bed. The high-ceilinged bathroom was huge with a wonderfully large walk in shower.

jeff hotel bedroom

The suites come with a kitchenette, flat screen tv, pour over coffee, clothes steamer and a Marshall amp speaker as well as some other fun design touches.

jeff hotel bathroom

Parking is at the nearby Water Street Garage which is a 5 minute walk from the hotel. Guests receive a parking voucher as part of their stay.

jeff hotel pastries

Whilst you could go and buy some food for breakfast, I highly recommend heading to the nearby Petite Mariebette instead.

NB: There is no elevator at the Jeff Hotel

If you’re more interested in the University of Virginia side of town, then look no further than The Oakhurst Inn. The Oakhurst Inn is about as close as you can get to the University after a dorm room. This unique property is spread across a cul de sac. Formerly it was the home of a university professor and three boarding houses.

Oakhurst Inn Cafe

In 2014, The Oakhurst Inn opened as a boutique hotel. It has 36 rooms, salt water pool and a lobby bar. The Oakhurst Inn is a 5 minute walk away and can service all of your breakfast needs – the outdoor space in the back is lovely.

Oakhurst Inn Pool

The lobby bar opens up to a comfortable lounge area made for grabbing a book and relaxing. The rooms are big, bright and airy and feature what I would call a modern classic New England style design theme eg oak floorboards, simple colours etc. The bathroom is a good size with a large walk in shower and Malin & Goetz toiletries.

Check Availability and Prices

Charlottesville has one of the most innovative and exciting wine scenes in the world today. I’ve been lucky enough to visit wineries in areas like Montepulciano , Mclaren Vale , Stellenbosch and more and seldom have I been as impressed with what was on offer. If you’re looking for an up and coming wine region Charlottesville is the place to visit!

Related Posts You Might Enjoy:

Where to taste wine in Livermore California

Best Wineries to Visit in Wolfville Nova Scotia

Things to do in Fredericksburg VA

Thanks so much to Visit Charlottesville and the Virginia Tourism Corporation for organising my fantastic visit to all these wonderful wineries in Charlottesville VA. They covered all of my costs on the ground eg accommodation, transport, most meals etc. I covered the cost of my flights. As always my opinions are my own.

Also, this wineries in Charlottesville VA post includes affiliate links. That means if you click through and end up making a purchase I will receive a small commission. I wanted to make sure you were aware of this.

IMG 2300 scaled

Amanda O’Brien is the creator and editor of The Boutique Adventurer. She has visited 80 countries and is a member of the British Guild of Travel Writers as well as the IFTWTA. She is passionate about wine had has just completed Level 3 of the WSET. Born in Australia, she lives in London.

This site uses Akismet to reduce spam. Learn how your comment data is processed .

Like this post? Why Not Share It?

Thanks for Sharing!

8 wineries to visit on the Monticello Wine Trail

As an appreciator of vineyards and wineries, I’ve made frequent excursions to winemaking areas in North Carolina. But several wine-expert friends said that I should also be looking a bit farther up the road for oenological getaways.

While Virginia has the same challenges and grows the same grapes as this state, several winemakers there are earning critical acclaim for their viogniers and cabernet francs.

Knowing where to start exploring can be daunting, though. Wine is booming in Virginia and there are now more than 250 wineries across the state. Of the seven AVAs, or American Viticultural Areas, the Monticello AVA established in 1982 was the first.

There’s also the historical significance as Thomas Jefferson was one of the first to experiment with growing European varieties in America at his Virginia estate. (The Monticello Wine Company won awards in Vienna and Paris in the 1870s.)

Today, the Monticello Wine Trail comprises 33 member wineries all within 25 miles of Charlottesville. In other words, way more than anyone can sip and swirl during a weekend. If you’d like some ideas where to start, here are a few cool wineries to check out.

Jefferson Vineyards (www.jeffersonvineyards.com)

One of the closest wineries to Monticello, it also has a long history of winemaking in the state. It’s now a third-generation family business that’s been recognized by Wine Spectator. You can also stay across the road, in the historic six-bedroom family home, Colle, rebuilt on the property in 1939. If you’d like a step up from the classic tasting, try the “Library Wine Tastings.” It’s $25 and includes some of the estate’s award-winning wines and a Riedel souvenir glass.

Barboursville Vineyards (www.bbvwine.com)

This winery near Gordonsville, Va., first started operating in the spring of 1976 under the direction of an Italian winemaking family. Visitors have a choice of the Tuscan Tasting Room, which is open every day of the week and is stocked with a range of current vintages, or Library 1821. The latter is open Friday through Monday and has tastings of a changing selection of older vintages, paired with bites from their chefs. There’s also an inn and Italian restaurant, Palladio, on site.

King Family Vineyards (www.kingfamilyvineyards.com)

Located in Crozet, Va., this large winery makes more than a dozen wines including its pink offering, Crosé, which is available in bottles and cans. It’s the perfect choice for summertime outside events. Like polo, maybe. The winery is home to the Roseland polo ground and visitors can sip wine and enjoy free matches each season beginning Memorial Day weekend through October. Bring a picnic, and a golf cart will drive by to make sure you have enough wine to enjoy with your meal.

Glass House Winery (www.glasshousewinery.com)

In addition to the great views and interesting wines, Glass House has a couple of features that set it apart from others on this list. A tropical conservatory, the titular glass house, is attached to the tasting room so you can sip surrounded by flowers and plants that include 12 varieties of bananas. One of the owners is also a chocolatier, and tastings often include a sample of one of the 10 varieties. Or you can buy a selection that includes the Earl Grey, Salted Caramel or Raspberry Champagne chocolates.

Blenheim Vineyards (www.blenheimvineyards.com)

This isn’t the only winery on this trail owned by a well-known person (there’s also the Trump Winery in Charlottesville), but it is the only one owned by a rock star. In this case, it’s Dave Matthews of the Dave Matthews Band. He purchased the winery in 1999 and helped design the winery building on site. The winery is known for unique labels, and you can buy prints and accessories with the logos and artwork as well. Check their calendar for upcoming events with food trucks and live music.

Early Mountain Vineyards (www.earlymountain.com)

If you’re short on time, you may want to make sure this winery is on your list. For one, their tasting room was named best in the country, according to a USA Today Readers Choice survey. Secondly, in addition to offering tastings of their own wines, they also serve a rotating, curated selection of wines made throughout the state. Look for flights like Cool & Crisp or Bouquet of Rosé in their ‘Best of Virginia’ program, which typically range in price from $20 to $22. You can also find a full menu in their tasting room, with dishes made from seasonal local produce.

Pollak Vineyards (www.pollakvineyards.com)

Pollak Vineyards is celebrating 11 years as a small family-owned winery in Greenwood, Va., that now has 31 acres of French grapes planted onsite. The tasting room and patio overlook the pond and nearby Blue Ridge Mountains. And, in colder months, there’s usually a fire going in the tasting room’s fireplace. Bring a picnic, or try their selection of cheeses, charcuterie and baguettes. They also host a Final Friday concert series during the season.

Knight’s Gambit Vineyard (www.knightsgambitvineyard.com)

If 33 wineries wasn’t daunting enough, there are also a few other wineries to be found in the region. Although not a member of the Monticello Wine Trail, this winery is a favorite with locals. It’s a family-owned winery, with family-produced artwork decorating the labels. There are usually an assortment of dogs that greet you in the tasting room, or out on the patio, who will keep you company while you sip the wines made on this solar-powered estate. Look for their live music events, and the Vinyasa, Vino & Views yoga series.

To learn more about the Monticello Wine Trail, go to monticellowinetrail.com. There, you can find a calendar of events at member wineries or make plans to attend the Taste of Monticello Wine Trail festival in the spring.

  • Featured Stories
  • Recipe Library
  • Drink Library
  • Restaurants
  • Print Subscription
  • The Local Palate Newsletters
  • Digital Edition Access
  • Marketplace

Recipe Issue Cover Thumbnail

subscribe now

Get our magazine for $25 a year

Give two gifts for the price of one! Only $24.99 a year

Recipe Issue Cover Thumbnail

Discover the best of

Southern food.

Plus, receive 10% off at the Local Palate Marketplace

TLP Logo Subscribe

Join The Local Palate's Virtual Cooking Club

An intimate, ticketed series event with esteemed chef, Maneet Chauhan cooking through her book,  Chaat .

Albemarle County Wine Country feat

20+ Award-Winning Wineries On the Monticello Wine Trail in Charlottesville & Albemarle County, Virginia

  • Copy to clipboard

Charlottesville and Albemarle County have 40+ wineries along the Monticello Wine Trail, and many of them are producing award-winning wines that are making wine aficionados from around the world take note. The 21 wineries listed here have won gold medals at the state’s premiere wine competition, the Virginia Governor’s Cup , and collectively, wineries on the Monticello Wine Trail received nearly half of all the gold medals awarded in 2023. Discover more about each award-winning winery and utilize the map feature to start planning your summer vineyard vacation!

Eastwood Farm and Winery

New to the Charlottesville winery scene, Eastwood Farm and Winery opened in 2020, and the woman-owned winery is already producing gold medal-winning wines. Visiting their property offers options galore including multiple indoor and outdoor spaces to sip their delicious vintages (along with house-made craft beer and cider), plus hiking trails and an on-site food truck. You’ll want to stay all day!

eastwood wines from Monticello Wine Trail

Cunningham Creek Winery

Family-owned and -operated, Cunningham Creek Winery welcomes everyone—kids and pets included! Enjoy award-winning wines while watching your dog run off-leash in the dog park, or relax with a wine and a picnic. Light snacks are available for purchase in the tasting room, and be sure to check the event page for live music, food trucks, and trivia.

Jefferson Vineyards

Purveyors of fine Virginia wines for more than 40 years, Jefferson Vineyards is a Charlottesville-area staple. The locale sits on the very same site where Thomas Jefferson and Filippo Mazzei began the first commercial vineyard in Virginia , an event pre-dating the Revolutionary War. Jefferson Vineyards has since bridged its traditions with modern viticulture practices to realize a dream nearly 250 years in the making.

Grace Estate Wines from Monticello Wine Trail

Grace Estate Winery

Focusing on agricultural tradition, Grace Estate Winery creates 100-percent estate grown Virginia wines at their 450-acre Mount Juliet Farm, winery, and tasting room. You may be sensing a theme: Virginia wine tasting experiences go hand in hand with breathtaking views, and Grace Estate is no exception. Plan to pack a picnic, and enjoy a lovely afternoon sipping award-winning wines and snapping some selfies throughout your experience.

Trump Winery

Planted with 227 acres of French vinifera varieties, Trump Winery is not only Virginia’s largest vineyard, but also the largest vinifera vineyard on the East Coast. A breathtaking 1,300-acre estate with an incredible vantage point which overlooks the beautiful rolling hills of the Charlottesville countryside. Enjoy wines by the bottle, glass, and flight, or enhance your visit by making a table reservation and pairing your selected varietals with artisanal menu items.

Afton Mountain Vineyards

Who wouldn’t want to sip award-winning wines in an all-weather glass pavilion while gazing at the Blue Ridge Mountains? Afton Mountain Vineyards’ vines were planted 45 years ago, making theirs some of the oldest in the state. Elevated at 1,000 feet on the eastern slope of Afton Mountain, the unique positioning of the vineyard allows grapes to thrive. And thrive they have, under the direction of winemaker Damien Blanchon, who has been at the helm for Afton since 2011.

King Family Vineyard Wines from Monticello Wine Trail

King Family Vineyards

Stewards of the land since 1998, King Family Vineyards is a family-owned and -operated winery now producing 10,000 cases per year. Classic and reserved tastings as well as vineyard tours are all options to gain a deeper understanding of the King Family wine program. If you’re visiting late spring through early fall, Sunday Polo at King Family is a tradition not to be missed.

Pollak Vineyards

All of Pollak Vineyards’ wines are fully estate grown from their 34 acres of French vinifera, which is all harvested by hand. Small batch, big flavor, and high quality is what you’ll find at Pollak. Cozy up by the fireplace in the tasting room on chilly days or bring a blanket and picnic near the pond during warm ones.

Stinson Vineyards

Inspired by garagiste winemaking in France, Stinson is unique in both its technique as well as its design: a renovated three-car garage designed by owner and architect Scott Stinson. Winemaking team Rachel Stinson Vrooman and Nathan Vrooman focus on European-style wine styles that emphasize subtlety and complexity. Enjoy a glass or bottle from the garage, featuring 360-degree mountain and vineyard views.

Stinson Vineyards from Monticello Wine Trail

Veritas Winery

Winemaker Emily Hodson’s philosophy is simple: allow the wine to show the beauty of where the grapes were grown, as well as a naturally balanced expression of the fruit by focusing on attention to detail and cultural practices. Hodson is one of just a few woman winemakers along the Monticello Wine trail who got her start in the Virginia wine industry and she has been at the helm for 15 harvests at Veritas. Plan a visit to enjoy these special varietals through a variety of experiences including tastings, food and wine pairings, picnics, and so much more.

Delfosse Vineyards and Winery

Celebrate with Delfosse on winning the Governor’s Cup this year! Hugged between the hills in Faber, Virginia along the Monticello Wine Trail, Delfosse enjoys the elevation to guarantee both flavorful wine and fabulous views. Tour their terraced vineyards (one of the only in Virginia), pack a picnic for outdoor lounging, or make a weekend of it when you book a stay in their 100-plus-year-old Historic Chestnut Log Cabin, a peaceful respite overlooking the lake.

Albemarle CiderWorks from Monticello Wine Trail

Albemarle CiderWorks

A testimony to the enduring appeal and viability of family farms and innovative agricultural enterprise, Albemarle CiderWorks is first and foremost a nursery, cultivating more than 250 apple varieties to curate their library of Virginia hard ciders. In addition to sustainability endeavors, Albemarle CiderWorks won best in show for cider at the 2023 Virginia Governor’s Cup. Reservations are encouraged for parties of any size wishing to visit Albemarle CiderWorks. Guided tastings are available in addition to ciders by the glass, flight, and bottle.

Michael Shaps Wineworks

By 1995, Michael Shaps had accumulated numerous awards and acquired a reputation as one of Virginia’s up-and-coming winemakers. Now, nearly 20 years later, Michael continues to be a leader in Virginia wine as both an innovator and entrepreneur. Shaps offers two tasting room experiences. 1650 Harris Creek Road features indoor and expansive outdoor seating and offers traditional tastings of the Michael Shaps Virginia wines, as well as the Maison Shaps Burgundy wines, imported from Michael’s winery in Meursault, France. Rustic and industrial, the Wineworks Extended tasting room is attached to the working warehouse and offers everyday drinking wines in the Wineworks label, including flights, wine on tap, growlers, carafes, and bottles.

Castle Hill Cider

Founded in 2010, Castle Hill Cider was born after its owners decided to take Castle Hill back to its orchard roots. Colonel Thomas Walker, the original owner of Castle Hill Estate—and Thomas Jefferson’s legal guardian—was the first to bring Newtown Pippin apple scions to Central Virginia following his return from the Battle of Brandywine in 1777. The variety was planted at Castle Hill and became known as the Albemarle Pippin apple. Today, the estate boasts some 5,000 cider apple trees growing 40-plus varieties. Cidermaker Don Whitaker aims to tell the tale of the terroir and history of the landscape in each glass of Castle Hill Cider. 

Nestled on 600 acres of rolling Virginia countryside is a stunning barn, which is home to the tasting room, production operation, and serves as a private event venue. Patio seating as well as groupings of Adirondack chairs dot the landscape while soft seating is available indoors. Hard cider by the glass, bottle, and flight is available as well as innovative cider cocktails and a light bites menu.

Toast at pippin hill

Pippin Hill Farm & Vineyards

A culinary vineyard, Pippin Hill’s focus is on garden- and vine-to-table and creating fine Virginia wine experiences. Quite possibly the most Instagrammed winery in the state, Pippin Hill offers a variety of ways to enjoy elevated food and wine, perfectly documenting it all the while. Tastings, estate tours, cooking and wine schools, and fine dining Vintners Table experiences featuring multi-course meals are all possibilities. For a more casual excursion, make a reservation to sip and dine in the tasting room overlooking the grounds with camera-ready Blue Ridge views in the distance.

Wisdom Oak Winery

Nestled on 126 acres, Wisdom Oak has multiple varietals planted including chardonnay, petit ,anseng, cabernet sauvignon, cabernet franc, and merlot. A small batch boutique winery, owners Jason and Laura Lavallee have crafted an “off the beaten path” experience, like those they have most enjoyed while visiting winemaking regions around the world.

Chestnut Oak Vineyard

Small, modern, and mighty is the perfect way to describe Chestnut Oak Vineyard. Producing small batches of red and white varietals, in a beautiful and vibrant setting, their goal is to provide a wonderful Virginia wine tasting. Bonus: seating areas provide an up-close-and-personal view of the grapevines, creating a truly immersive experience. Plan a weekend visit to enjoy a picnic with friends on their lovely grounds or add it to your Monticello Wine Trail itinerary.

Keswick Vineyards

Dedicated to creating superior wines, Keswick Vineyards invites you to enjoy a relaxing afternoon on the covered porch or bring a picnic to enjoy al fresco while sampling some of its exclusive tasting room selections. New to the Keswick experience is a mini golf course, complete with wine barrels throughout to hold your glass. Beer and cider offerings round out the experience—Keswick truly offers something for everyone.

Wine from Hawk Vineyards

Hark Vineyards

Sustainability, great views, and wine all in one place! As outdoor lovers, Aaron and Candice Hark were careful to cultivate the land with both gathering spaces and places of quietude in mind. They also installed a 103-kilowatt solar panel system atop the winery building’s roof, which will offset 3.7 million pounds of carbon dioxide over the next 25 years. Enjoy wine and a BYO picnic (fire pits are available during the winter) or purchase cheese, crackers, and even chocolate at the tasting room.

Barboursville Vineyards

Luca Paschina, Barboursville’s resident winemaker for more than 30 years, holds the most diverse and extensive record of honors among all his peers in Virginia. According to Luca, “the estate of wine is a divine gift without borders, linking humanity and our diverse cultural backgrounds to their most elemental and their most celebratory nourishment.” Considered one of the leading wineries in Virginia, and also one of the oldest, Barboursville wine was selected to be served to Queen Elizabeth II during her 2007 visit to Virginia. Discover the newest vintages in the tasting room, then purchase a glass and enjoy a historic stroll around the Barboursville Ruins; Thomas Jefferson’s mansion for Governor James Barbour which was mostly destroyed by a fire on Christmas Day 1884. 

Sip cellared vintages alongside culinary pairings in the Library 1821 as you overlook an expansive slope of cabernet franc vines and the Blue Ridge Mountains.

Moss Vineyards

Dramatic views and design alongside delectable wine—and cider—is what you’ll find at Moss Vineyards. Atop the mountain in Dyke, Virginia, Barry and Ellen Moss have created quite the getaway featuring small batch, estate grown wines and now a dry cider (the gold medal winner) for guest enjoyment. You’ll want to come prepared with outside food since you’ll be in no rush to leave this fairytale location.

With a bounty of wineries along the Monticello Wine Trail, it’s worthwhile to plot out your route and visit a few each day. Never fret, many of the wineries listed above offer on-site lodging with breathtaking landscapes ranging from lush open fields to the Blue Ridge Mountains. All you have to do is sit back, sip, and drink in the sunset before heading out to your next destination on the trail. Start planning your summer stay today at www.visitcharlottesville.org !


TLP's Partners

Leave a reply cancel reply, be the first to comment..


Ctra. de Sant Sadurni a Ordal, Km.4 Els Casots – 08739 Subirats – Barcelona Tel. +45 145 66 37



Wintergreen Resort

Discover monticello wine tours: a perfect excursion for wintergreen resort guests.

Nestled in the heart of Virginia’s picturesque landscape within the Blue Ridge Mountains, Wintergreen Resort is a haven for ski, snowboarding, outdoor, mountain-biking enthusiasts, or the weekender looking for the perfect stop off the Blue Ridge Parkway. But what if skiing isn’t on your agenda? At the foot of the four season Wintergreen Resort, is over 50 wineries and breweries, and noteworthy, a wine region voted by Wine Enthusiast,  American Wine Region of 2023.

The Allure of the Monticello Wine Trail in the Blue Ridge Mountains

Monticello, renowned as the birthplace of American viticulture, boasts a rich history and prestige in winemaking. This legacy dates back to Thomas Jefferson, who envisioned Virginia as a wine-producing region. The very first grapes planted in the United States, were by Thomas Jefferson an estate (vacation rental managed by Stay Charlottesville) called Colle, just minutes from Jefferson’s home Today, Monticello’s wine country is a testament to his vision, offering a variety of wines that cater to every palate, from robust reds to crisp whites.

The scenic beauty of Blue Ridge Mountains and vineyards adds to the allure of these tours. As you traverse through rolling hills and lush landscapes, the picturesque views provide a serene backdrop that contrasts the adrenaline-fueled slopes of Wintergreen Resort. It’s an invitation to slow down and savor the moment, making it a perfect retreat for those seeking a break from the ski runs.

Wine Tours or Skiing, that is the ?

While skiing is a thrilling activity, wine tours offer a different kind of adventure – one that relaxes the mind and tantalizes the senses. These tours are not just about wine tasting; they are a cultural journey. Visitors get an insight into the art of winemaking, learning about local grape varieties, vineyard management, and the intricacies of fermentation. It’s an educational experience that also allows you to connect with local history and traditions.

While the resort is a four season mountain resort, winter tours offer their own charm, with fewer crowds and a serene, frost-kissed landscape. Moreover, Monticello Wine Tour can take you safely to enticing dining options, live music at the vineyards, and are accessible to a wide range of people. Whether you’re a couple looking for a romantic getaway, a group of friends seeking a new experience, or a family with older members, these tours cater to all. Unlike skiing, which requires a certain level of physical fitness and skill, wine tours are a leisurely activity that everyone can enjoy.

What to Expect on a Monticello Wine Tour

Monticello Wine Tours picks up at Wintergreen Resort at no extra cost. Thus far, we are the only wine tour operator from Charlottesville that does not charge additional fees to pick up on top of this Blue Ridge mountain.

Each tour is custom, providing an opportunity to visit multiple vineyards or breweries, each with its distinct charm and specialties, which our award winning team fully understand.

A typical route involves a visit to several wineries and usually last 5 hours, where guests partake in tasting sessions. Stop at the resort coffee shop first, tours usually begin at 10:30 or 11. These sessions are not just about sipping wine; they’re an exploration of flavors and aromas, guided by knowledgeable staff who provide insights into each wine’s profile. Many tours also include food pairings, offering a taste of local cuisine that complements the wines.

Wintergreen wine tour with friends

Lastly, Monticello Wine Tour only operates Mercedes Sprinter Vans or Chevrolet Suburbans with panoramic sunroofs, the most modern fleet with the most modern amenities. Please note, while Wintergreen Resort is next to the Blue Ridge Parkway, we are not allowed to use the parkway as a route. Additionally, often the parkway is not open in the winter post winter storms.

Planning Your Visit

The best times to embark on a wine tour are when you do not plan in partaking in Wintergreen’s championship golf, award winning tennis program, terrain park, spa, or snow tubing. Wintergreen resort is also well known for its event space and as a great conference spot for meetings. In the hours you’re not enjoying the aforementioned, we can help you plan a tour lasting for hours. We offer special rates for resort/meeting guests requiring more than 1 van during Monday- Friday hours.

Booking a tour is straightforward. Guests can either book directly through  Monticellowinetour.com  or through our full service concierge team 434-260-7143. Transportation options are plentiful, with many tours offering pick-up and drop-off services from the mountain, ensuring a hassle-free experience.

Monticello wine tours present a delightful alternative for Wintergreen Resort guests. They offer a chance to unwind, learn, and indulge in the finer things in life. Whether you’re a wine connoisseur or new to the world of wines, these tours promise an unforgettable experience.

So, if you’re staying at Wintergreen Resort and looking for an activity beyond the ski slopes one afternoon, consider a journey into the heart of Virginia’s wine country. It’s an adventure that will leave you with lasting memories and a newfound appreciation for the art of winemaking.

About Wintergreen Resort

Wintergreen Resort is one of two resorts well-known for skiing within Virginia, the other being Massanutten. The main base of the mountain is known as the Mountain Inn, where you will check-in for your rentals. Open for group business with ample event space, and being located just three hours from Washington, two hours from Richmond, Wintergreen is a great full service option for corporate retreats. Wintergreen hosts homes, condominiums, and hotel rooms for accommodations, most with a fully equipped kitchen

Wintergreen Activities and Excursions

Wine, then dine and unwind. Guests of the Monticello Wine Tour receive complimentary access within one day (+/-) of booked transportation to Common House, a modern social club on Charlottesville’s Downtown Mall.


Wine and Country Life

  • Virginia Wine & Country Life
  • Read the Current Issue
  • Visit Virginia
  • Food & Drink
  • Home & Garden
  • Dream Properties
  • Style & Culture
  • Experiences
  • Business Events

2022 Monticello Cup Awards Charlottesville Winery

Food & Drink

Announcing the best of the monticello wine trail.


words by Frank Morgan | Photos by R.L. Johnson

After a two-year hiatus, the local wine industry gathered in-person on April 26th at the Common House in Charlottesville to celebrate and recognize the winning wineries from this year’s Monticello Cup Wine Competition. Laura and Jason Lavallee of Wisdom Oak Winery won the 2022 Monticello Cup for their NINETEEN, a Bordeaux-style red blend. NINETEEN bested 73 other entries to win the region’s top wine honor.

2022 Monticello Cup Awards Charlottesville Winery frank morgan

Top left: Frank Morgan, the event organizer and celebrated wine author, tastes one of the gold-winning white wines. Top right and bottom left: wine industry professionals mingle at the first in-person event in two years, renewing acquaintances and tasting the gold-winning wines.

This marks the 31st year for the annual competition held by the Charlottesville-area’s Monticello Wine Trail, a subsidiary of the Jeffersonian Wine Grape Growers’ Society. This is the first Cup win for the Lavallees and Wisdom Oak Winery, but it follows a continued streak of awards for their wines.

“Winning the Monticello Cup means everything to us and our team,” said Jason Lavallee. “Not having a winemaking background and only doing this for a few years makes winning the Monticello Cup even more special for us.”

Tracing Charlottesville’s Monticello Wine Trail

Stephen Barnard, winemaker at Keswick Vineyards and current president of the Monticello Wine Trail, said the annual competition puts the spotlight on some of the best wines being made in the Monticello AVA and helps raise consumer interest in local wineries .

From sparkling wine to crisp white wines, elegant reds like Cabernet Franc to big bold Meritage blends, the top scoring wines showcase the quality and grape diversity of the Monticello region.

“I am so excited to see so many varied styles and varieties being made on a world class level and extend my heartiest congratulations to all the deserved winners,” said Barnard.

The Monticello Wine Trail is home to about 40 wineries situated across the central Piedmont, all within about 25 miles of Charlottesville, Virginia and spanning Albemarle, Fluvanna, Greene, Nelson and Orange counties.

Established in the early 1980s, the Monticello Wine Trail is a subset of the Jeffersonian Wine Grape Grower’s Society. As part of the Taste of the Monticello AVA Week, a Red Wine Showcase was held at Eastwood Farm & Winery.

2022 Monticello Cup Awards Charlottesville Winery. The winemakers of Stinson, Flying Fox, Veritas ,Hark Winery, Blenheim Vineyards

The Wine & Country team had a moment to talk with some of the leading women of Virginia winemaking. From the left: Emily Hodson of Veritas Vineyards & Winery and Flying Fox Vineyards ; AJ Greely of Hark Vineyards; Kirsty Harmon of Blenheim Vineyards ; Dr. Joy Ting of Virginia Winemakers Research Exchange; and Rachel Stinson Vrooman of Stinson Vineyards.

The Monticello American Viticultural Area

The Monticello American Viticultural Area (AVA) encompasses Charlottesville wineries and is named in honor of Thomas Jefferson’s Charlottesville home at Monticello where he worked to establish vinifera vineyards with Filippo Mazzei in the 1770s. They hoped that Virginia could become a wine making area, creating wine on par with those he enjoyed in the Old World while traveling as Minister to France. Though the American Revolution interrupted their viticultural pursuits and environmental factors further stymied them, they’d clearly be delighted to see today how the Monticello AVA is carrying out their dreams of producing world class wines.

“We could, in the United States, make as great a variety of wines as are made in Europe,” wrote Jefferson in 1808, “not exactly of the same kinds, but doubtless as good.”

The Monticello AVA is Virginia’s oldest, established in 1984, and covers roughly 800,000 acres of the Central Piedmont including most of the counties of Albemarle, Fluvanna, Greene, Orange and Nelson all within approximately 25 miles of Charlottesville. Growing over 30 varieties of grapes, the Monticello AVA is most noted for Cabernet Franc, Petit Verdot, Merlot, Chardonnay, Cabernet Sauvignon and Viognier which is often noted as the area’s signature grape, well developed by the wine pioneers at Horton Vineyards .

Tucked into the Eastern slopes of the Blue Ridge Mountains and including the small ridge known as the Southwest Mountains, the hardiness zone of the Monticello AVA is 7a except in some higher vineyards which are 6b. The warm summers and the wind protection of the mountains contribute to success in the vineyards’ expression of terroir. Soil types range widely from fertile, silty loams to heavier clay-based soils rich in granite. The greatest challenge in the climate is warm and humid summers, which are managed by extensive canopy work, trellising and pruning techniques that can even be block specific on some properties. Winter freezes and late frosts after bud break also challenge viticulturists, leading to careful site selection, often at altitudes of 800 feet and up.

2022 Monticello Cup Awards Charlottesville Wisdom Oak Winery

Judging the 2022 Monticello Cup

26 Charlottesville area wineries entered a total of 74 wines into this year’s competition. Each winery was limited to submitting three wines, all of which must contain at least 85% grapes grown in the Monticello American Viticultural Area (AVA). 22 of those 74 wines scored 90+ points, earning a gold medal, while 47 won silver and 5 won bronze medals.

Judging took place in early March at King Family Vineyards in Crozet. 10 wine professionals performed a blind taste test in two rounds—a preliminary round and a final round. The top 12 scoring wines from the preliminary round were re-tasted and scored in the final round to determine the winners.

The esteemed panel of judges included Robert Jones, Master of Wine; Aileen Sevier, Vice President, Early Mountain Vineyards; Michael Kimball of Consociate Media; Paul Ting, writer; Lance Lemon, owner of the online wine shop RichWine; Megan Hereford of Scott Labs; Booth Hardy, owner of Barrel Thief Wine Shop; Lindsey Parris, Capital Wine School; Becca Yeamans, writer; and, Adam Caperton, Winebow.

2022 Monticello Cup Awards Charlottesville Winery veritas flying fox

Top left: Elliot Watkins and the team from Veritas Vineyards and Winery and Flying Fox Vineyards. Bottom left: Jefferson Vineyards was the only winery to win a place in both the Top 3 Reds and Top 3 Whites. To the right, Wine & Country Life Editor-in-Chief Jennifer Bryerton talks with gold-winning Luca Paschina of Barboursville Vineyards about newly planted vineyard blocks.

Top 3 Red Wines of the Monticello Wine Trail

Wisdom oak winery 2019 nineteen.

A Bordeaux blend of the best barrels in the 2019 vintage as selected by the winemaker. Bold, full-bodied red wine made from estate grown fruit. 50% Petit Verdot, 25% Cabernet Sauvignon, 25% Cabernet Franc. Wonderful structure and concentration from one of the best vintages Virginia has ever seen.

Cardinal Point Vineyard & Winery 2019 Clay Hill Cabernet Franc

Cardinal Point winemaker Tim Gorman, who won the Monticello Cup in 2017, continues to impress with wines such as the expressive and aromatic Cabernet Franc.

Jefferson Vineyards 2019 Merlot Reserve

Jefferson Vineyards scored two top spots with traditional varieties: Chardonnay and Merlot. Though both grapes are often overlooked for newer styles and grapes, both Chardonnay and Merlot are used to make some of the region’s best and most expressive wines.

Top 3 White Wines of the Monticello Wine Trail

Michael shaps wineworks 2019 petit manseng.

Perennial Cup contender Michael Shaps, who makes wine at his eponymous winery in Charlottesville, Shenandoah Vineyards and in the Burgundy region of France, scored a top spot again this year with his 2019 Petit Manseng.

Shaps was one of the first winemakers in the state to embrace the small-berried, thick-skinned grape from the Jurancon region of southwestern France that’s become one of the most fashionable grapes today.

Jefferson Vineyards 2019 Chardonnay Reserve

Light toast and spice are greeted with elegant flavors of pear and apple. This balanced, well-integrated wine finishes with citrus notes and great length.

Trump Winery 2017 Blanc de Blanc

Winemaker Jonathan Wheeler scored a top-three spot again this year with the Trump Winery 2017 Blanc de Blanc, a traditional method sparkling wine made from Chardonnay.

Meet Wisdom Oak Winery’s Owners

Jason is the winemaker, and Laura operates the tasting room and all other phases of the winery. Life amongst the vines in the rolling hills of North Garden is quite a way from Cape Cod, where Mr. Lavallee grew up, and rural Maryland, where Mrs. Lavallee was raised. The couple met over a decade ago in Philadelphia while working in the financial services industry. They bonded over their shared love of food and wine, which brought them to Virginia to explore local wineries at the suggestion of a friend. During one of their trips, they decided to move to Virginia from Philadelphia. In 2015, on the day before Thanksgiving, they purchased the 126-acre farm known as Sugar Leaf Vineyards that would ultimately become Wisdom Oak Winery.

“Winning the Monticello Cup means everything to us and our team. Not having a winemaking background and only doing this for a few years makes winning the Monticello Cup even more special for us.”

2022 Monticello Cup Awards Charlottesville Wisdom Oak Winery

Laura and Jason Lavallee of Wisdom Oak Winery accept the Monticello Cup on behalf of their 2019 NINETEEN Bordeaux Blend.

Opening Wisdom Oak Winery as a Second Job

Laura and Jason maintained their day jobs in the financial industry for 18 months while working to establish Wisdom Oak Winery. Though the couple has no formal viticulture or winemaking training, they are quick studies—they’ve built a thriving winery via hands-on learning and sweat equity. They credit the generosity of exceptional local winemakers including Matthieu Finot of King Family Vineyards and other vineyard teams for sharing valuable knowledge to help navigate the steep viticulture and winemaking learning curve.

Today, the Lavallees farm six acres of vines at their Wisdom Oak Winery estate vineyard and have 14 acres under vine at Bundoran Farm, situated three miles east of their winery, and produce about 4,000 cases of wine.

2022 Monticello Cup Awards Charlottesville Wisdom Oak Winery

NINETEEN, Wisdom Oak Winery’s 2022 Monticello Cup Winner

A blend of 50% Petit Verdot, 25% Cabernet Franc and 25% Cabernet Sauvignon, NINETEEN is named for the 2019 vintage, widely considered one of the best in Virginia in recent years, especially for reds.

“Our fruit in 2019 was excellent,” said Jason. “It was so good I wrote ‘beast’ on the best barrels because I knew it was going to be a beast of a wine.”

A beast of a wine for sure. The bold and structured NINETEEN has garnered top scores in other important competitions, such as the Virginia Governor’s Cup .

2022 Monticello Cup Awards Charlottesville Wisdom Oak Winery

Wisdom Oak Winery’s other vintages haven’t been idle, either. Their 2017 Petit Manseng won a Double Gold award in the prestigious San Francisco International Wine Competition . Their 2018 vintage of the same wine won Best in Category in the 2019 Atlantic Seaboard Wine Competition .

Jason credits a good amount of the success of NINETEEN to the excellent growing conditions of that year. It was a very dry year, resulting in very concentrated flavors in the grapes. Four barrels in particular were given Jason’s coveted “beast” title. Having such quality fruit allowed for more options to experiment with blends, which ultimately resulted in this award-winning wine.

“We finally had the winery put together, and then in ’18 we got rained out,” Jason recalls. “In ’19 it’s like, ‘it’s time to shine’—and man, did it shine.”

Monticello Cup Gold Medalists

In alphabetical order by winery, here are the Gold Medal wines from the 2022 Monticello Cup Wine Competition:

  • Afton Mountain Vineyards (2) – 2017 Bacco, 2017 Tradition
  • Barboursville Vineyards (2) – 2014 Octagon, 2019 Nebbiolo Reserve
  • Cardinal Point Vineyard & Winery (1) – 2019 Clayhill Cabernet Franc
  • Chestnut Oak Vineyard (2) – 2016 Cabernet Sauvignon, 2017 Chestnut One
  • DelFosse Vineyards and Winery – 2020 Go Go Girl
  • Flying Fox Vineyard (2) – 2017 Petit Verdot, 2017 Trio
  • Hark Vineyards (1) – 2019 Merlot
  • Jefferson Vineyards (2) – 2019 Merlot Reserve, 2019 Chardonnay Reserve
  • Keswick Vineyards (1) – 2019 Estate Reserve Cab Sauv Block 7
  • Michael Shaps Wineworks (1) – 2019 Petit Manseng
  • Pollak Vineyards (1) – 2019 Meritage
  • Stinson Vineyards (1) – 2017 Meritage
  • Valley Road Vineyards (1) – 2019 Cabernet Franc
  • Veritas Vineyard & Winery (2) – 2017 Veritas Reserve, 2017 Petit Verdot
  • Wisdom Oak Winery (1) – 2019 NINETEEN
  • Trump Winery (1) – 2017 Blanc de Blanc

To see who won the Cup in recent years, read more on the 2020 Monticello Cup Winners . For other award-winning Virginia wines, stop by the  Wine & Country Shop  in Ivy. Open Virginia Wine Day is coming soon – consider making yours an award winning bottle. ~

FRANK MORGAN writes a wine column for The Virginian-Pilot newspaper and is author of the DrinkWhatYouLike.com wine blog, started thirteen years ago to chronicle his wine travel experiences and to share stories of the wines, wineries, and winegrowers of Virginia. He also serves as the organizer of the Monticello Cup Wine Competition and the Shenandoah Valley Wine Competition and is a final round judge for the Virginia Governor’s Cup. He lives in Chesapeake, VA, with his wife and daughter.

R. L. JOHNSON  is our co-publisher and creative director, Robin Johnson Bethke, who began her career as a professional photographer in Los Angeles before moving into graphic design and art direction when she relocated to Charlottesville in 1994. As our company’s co-founder and visionary, she enjoys all aspects of the publishing process from story conception to graphic design to photography. Her work is often seen in many of our publications.

you might like

Cana Vineyards Wins 2022 Governor's Cup

Best Wines of Virginia in 2022

monticello wine trail tour

Sharon Horton Wins Monteith Award

monticello wine trail tour

2020 Monticello Cup Winners

Horton Vineyards, cabernet franc, Virginia. Image by © RL Johnson for Virginia Wine & Country Life.

Virginia Wineries Making the Best Cabernet Franc

monticello wine trail tour

Virginia Wine & Country celebrates elevated living in Virginia Wine Country. Virginia Wine & Country Life is a semi-annual luxury print magazine with a full digital presence. The Virginia Wine & Country Gold Book is an annual guide to the top award-winning wines, wineries and experiences in Virginia Wine Country. The annual Virginia Wine & Country Wedding Planner is an art book of elegant Virginia weddings. Virginia Wine & Country tells the stories of Virginia wineries, the farm-to-table movement, luxury travel, entertaining, art and the elegant country lifestyle. Ivy Life & Style Media  also provides branding, web design and PR services for the wine industry.

Privacy Overview

Friend's Email Address

Your Email Address


  1. The Best Charlottesville Wineries on the Monticello Wine Trail

    monticello wine trail tour

  2. See what happens when a Virginia wine club takes a drive through the

    monticello wine trail tour

  3. Monticello Wine Trail: A Wine-Filled Day Trip From Richmond, Virginia

    monticello wine trail tour

  4. Gallery

    monticello wine trail tour

  5. Monticello Wine Trail

    monticello wine trail tour

  6. The Best Charlottesville Wineries on the Monticello Wine Trail

    monticello wine trail tour


  1. Monticello Wine Trail

    The Monticello Wine Trail consists of more than 30 beautiful wineries all within easy access of Charlottesville. Start planning your weekend of wine tasting or come for the day. Meet a winemaker, enjoy a wine festival, or a concert under the stars, these are but a few of the many attractions you can enjoy with a visit to the Monticello Wine Trail.

  2. Monticello Wine Tour & Coach Co

    Private 5 hour wine/brewery tour for Group up to 14 Passengers (ability to add additional hours) Book Now Testimonials What people are saying about their time with us. Looking for a great place to STAY! Explore STAY CHARLOTTESVILLE ACCOMMODATIONS 100 Second St NW Suite F Charlottesville, VA 22902 Tel. +1 434.260.7143 FB IG

  3. The Best Charlottesville Wineries on the Monticello Wine Trail

    There are 33 wineries on the Monticello Wine Trail that all span near the Blue Ridge Mountains. The Blue Ridge Mountains and Charlottesville are two of the best places to visit in Virginia. So with a great glass of wine and the vibrant Blue Ridge Mountains, you can guarantee you will be surrounded by great beauty.

  4. Follow the Monticello Wine Trail: Your Guide to Charlottesville Wineries

    The Monticello Wine Trail has 40+ wineries within a 25-mile radius of Charlottesville to sip and savor, with much more to do and see. From nearby hiking trails and local businesses to beautiful bed and breakfasts and resorts, the Monticello region is full of beautiful experiences across Virginia's wine country.

  5. Explore the Monticello Wine Trail in Virginia

    On the Monticello Wine Trail, explore Virginia's bucolic countryside. Sample the regional wine from some of the best Charlottesville wineries, meet the winemakers, and take in Virginia's rich cultural history. With many vineyards and wineries to choose from, this shortlist includes historic vineyards, wineries and a cidery.

  6. Our Guide to Visiting the Monticello Wine Trail

    While we have shared some of our favorite wineries across both Charlottesville and Central Virginia in previous posts, this is our guide to visiting the Monticello Wine Trail, an active association of wineries, all within 25 miles of Charlottesville, Virginia.We can personally attest to these places and their wines, as these are some of our favorite wineries to stop by when we're in the area.

  7. Guide to Virginia's Monticello Wine Trail

    The Monticello Wine Trail currently consists of 33 of the best wineries in Virginia and is a definite must see if wine is what gets your juices flowing. History of the Monticello AVA and wine trail The Monticello AVA is the first established AVA of Virginia.

  8. Monticello Wine Trail

    Western Trail: Afton Mountain Vineyards Cardinal Point Vineyard & Winery Pollak Vineyards Flying Fox Vineyard Veritas Vineyard & Winery Eastern Trail: Barboursville Vineyards Burnley Vineyards Chestnut Oak Vineyard Horton Vineyards Keswick Vineyards Reynard Florence Vineyard Southern Trail: Jefferson Vineyards Blenheim Vineyards First Colony ...

  9. 5 Must-Visit Wineries on the Monticello Wine Trail

    And once you're in, you get a chance to sample exquisite craft winemaking from the renowned Michael Shaps. In a nutshell, Pippin Hill is the place to go for an all-around experience. Tasting Price: $10 per person. Address: 5022 Plank Road, North Garden, VA 22959 (Tel: 434-202-8063).

  10. Monticello Wine Tour & Coach Co.

    Monticello Wine Tour & Coach Company is a local transportation and guide service offering tailored wine tours and travel experiences in Charlottesville, Albemarle, and the surrounding regions.

  11. Wine Tours Charlottesville

    The Monticello Wine Trail is Virginia's crown-jewel, truly fulfilling Thomas Jefferson's vision of wine-making in Virginia. Norm's Transportation offers a variety of tours to Charlottesville area wineries. You can choose and customize your tour from the wineries listed below OR pair a couple of wineries with a historic attraction if you'd like.

  12. Private Wine and Beer Tours

    1 2 Private 5 hour wine/brewery tour for Group up to 6 Passengers (ability to add additional hours) Sunday-Friday $87.10/hr. Saturday: $95.00/hr (5 hr. min.) Book Now Mercedes Sprinter Van Private 5 hour wine/brewery tour for Group up to 11 Passengers (ability to add additional hours) Sunday-Friday: $103.00/hr. Saturday: $121.10/hr (5hr min.)

  13. 15 Wineries in Charlottesville Va You'll Love I Monticello Wine Trail

    Wine flights are on offer as are wines by the glass and bottle. 13. Barboursville Vineyards. Barboursville Vineyards is one of the oldest wineries on the Monticello Trail. Run by three Italian brothers it came up frequently during my trip as one of the best Charlottesville wineries to visit.

  14. Monticello Wine Trail Tour

    Saturday, June 25, 2022 Visit the historic Monticello Wine Trail! This fun-filled ALL-INCLUSIVE day tour departs from Virginia Beach & Downtown Hampton, VA and includes round-trip bus transportation, complimentary continental breakfast, mimosas, live historical entertainment, wine tastings and tours at family owned vineyards, lunch at 18th century Michie Tavern, located 1/2 mile from ...

  15. Book Tour

    Eastern Shore Wine, Brine & Casino Trail Tour - Dec 30, 2023 $300.00 $224.99 Saturday, December 30, 2023 ALL INCLUSIVE day of wine, food, and casino fun as we bring history to life! Relax and travel to the historic Eastern Shore of Virginia where the Atlantic Ocean meets the Chesapeake Bay.

  16. Monticello Wine Trail

    Monticello Wine Trail, Charlottesville, Virginia. 5,151 likes · 101 talking about this. The Monticello Wine Trail: Over 40 beautiful wineries comprising...

  17. 8 wineries to visit on the Monticello Wine Trail

    Today, the Monticello Wine Trail comprises 33 member wineries all within 25 miles of Charlottesville. In other words, way more than anyone can sip and swirl during a weekend. If you'd like some...

  18. Monticello Wine Trail Tour

    Saturday, May 18, 2024 Visit the historic Monticello Wine Trail! This fun-filled ALL-INCLUSIVE day tour departs from Virginia Beach & Downtown Hampton, VA and includes round-trip bus transportation, complimentary continental breakfast, mimosas, gift bags, live historical entertainment, wine tastings and tours at family owned vineyards, lunch at 18th century Michie Tavern, located 1/2 mile from ...

  19. Award-Winning Wines on Monticello Wine Trail

    Award-Winning Wines on Monticello Wine Trail - The Local Palate Partnered 20+ Award-Winning Wineries On the Monticello Wine Trail in Charlottesville & Albemarle County, Virginia By: TLP's Partners

  20. Experience the Finest Wintergreen Resort Wine Tours

    The Allure of the Monticello Wine Trail in the Blue Ridge Mountains. Monticello, renowned as the birthplace of American viticulture, boasts a rich history and prestige in winemaking. This legacy dates back to Thomas Jefferson, who envisioned Virginia as a wine-producing region. ... Monticello Wine Tour. Monticello Wine Tours picks up at ...

  21. Announcing the Best of the Monticello Wine Trail

    The Monticello Wine Trail is home to about 40 wineries situated across the central Piedmont, all within about 25 miles of Charlottesville, Virginia and spanning Albemarle, Fluvanna, Greene, Nelson and Orange counties. Established in the early 1980s, the Monticello Wine Trail is a subset of the Jeffersonian Wine Grape Grower's Society.